USPatentGranted
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1-cycloalkylpyrazolyl-benzoyl derivatives

Granted 30 Mar 2004 · 2 office actions

Current assignee: BASF Aktiengesellschaft · originally BASF SE

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Inventors: Guido Mayer, Klaus Langemann, Helmut Walter, Roland Gtz +9 · Examiner: Alan L. Rotman · AU 1626 · TC 1600

Application
10/048,949
filed 1 Dec 1999
Publication
Not published
not published
Patent· this page
US 6,713,436
granted 30 Mar 2004

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Abstract

The present invention relates to 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I wherein all variables are as defined in the specification, their agriculturally useful salts, processes for their preparation, and for the use of these compounds or compositions comprising them, for controlling undesirable plants.

Description

15 parts
›This application is a 371 of PCT/EP99/09342 filed…

This application is a 371 of PCT/EP99/09342 filed Dec. 1, 1999.

The present invention relates to 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I

where:

X is O, NR 6 or CR 7 R 8 ;

Y is O, S, NR 9 or CR 10 R 11 ;

R 1 is nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfonyl or C 1 -C 4 -haloalkylsulfonyl;

R 2 ,R 3 ,R 7 ,R 8 ,R 10 ,R 11 are hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl;

or

R 3 and R 6 or R 3 and R 8 or R 3 and R 9 or R 3 and R 11 together form a bond;

R 4 is halogen, nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfonyl or C 1 -C 4 -haloalkylsulfonyl;

R 5 is hydrogen, halogen or C 1 -C 4 -alkyl;

R 6 ,R 9 are hydrogen or C 1 -C 6 -alkyl;

R 12 is hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy;

R 13 is a cyclic ring system containing 3 to 14 ring atoms which may be partially or fully halogenated and/or may carry one to three of the following groups: C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy;

R 14 is hydrogen or C 1 -C 4 -alkyl;

and their agriculturally useful salts.

Moreover, the invention relates to processes for preparing compounds of the formula I, to compositions comprising them and to the use of these derivatives or of compositions comprising them for controlling harmful plants.

Cycloalkyl-substituted pyrazolylbenzoyl derivatives which are substituted in the 3-position of the benzoyl radical by an N-bonded heterocycle or by phenyl are disclosed in the literature, for example in WO 98/42678 and WO 98/52926.

However, the herbicidal properties of the prior art compounds and their compatibility with crop plants may not be entirely satisfactory.

It is an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.

We have found that this object is achieved by the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.

Depending on the substitution pattern, the compounds of the formula I may contain one or more chiral centers, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I can also be present in the form of their agriculturally useful salts, the kind of salt usually being immaterial. In general, the salts of those cations or the acid addition salts of those acids are suitable whose cations and anions, respectively, do not adversely affect the herbicidal action of the compounds I.

Suitable cations are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced here by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl, preferably ammonium, dimethylassonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-ylammonium, di(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C 1 -C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(C 1 -C 4 -alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic molecular moieties mentioned for the substituents R 1 -R 12 or as radicals on phenyl rings are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkylcarbonyl, haloalkyl, alkoxy, haloalkoxy, alkylcarbonyloxy, alkylsulfonyloxy, alkylthio, haloalkylthio, alkylsulfonyl, haloalkylsulfonyl, alkenyl and alkenyloxy moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine or iodine.

Examples of other meanings are:

C 1 -C 4 -alkyl, and the alkyl moieties of C 1 -C 4 -alkylcarbonyl and C 1 -C 4 -alkylcarbonyloxy: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl;

C 1 -C 6 -alkyl, and the alkyl moieties of C 1 -C 6 -alkylcarbonyl and C 1 -C 6 -alkylcarbonyloxy: C 1 -C 4 -alkyl as mentioned above, and also, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl;

C 1 -C 4 -haloalkyl: a C 1 -C 4 -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoramethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromoethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl;

›C 1 -C 4 -alkoxy: for example methoxy…

C 1 -C 4 -alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy;

C 1 -C 6 -alkoxy: C 1 -C 4 -alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy;

C 1 -C 4 -haloalkoxy: a C 1 -C 4 -alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;

C 1 -C 4 -alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;

C 1 -C 4 -haloalkylthio: a C 1 -C 4 -alkylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio and nonafluorobutylthio;

C 1 -C 4 -alkylsulfonyl (C 1 -C 4 -alkyl-S(═O) 2 -), and the alkylsulfonyl moieties of C 1 -C 4 -alkylsulfonyloxy: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl and 1,1-dimethylethylsulfonyl;

C 1 -C 6 -alkylsulfonyl, and the alkylsulfonyl moieties of C 1 -C 6 -alkylsulfonyloxy: a C 1 -C 4 -alkylsulfonyl radical as mentioned above, and also, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl;

C 1 -C 4 -haloalkylsulfonyl: a C 1 -C 4 -alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2,2-difluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-difluoropropylsulfonyl, 2,3-difluoropropylsulfonyl, 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl, 2,2,3,3,3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1-(fluoromethyl)-2-fluoroethylsulfonyl, 1-(chloromethyl)-2-chloroethylsulfonyl, 1-(bromomethyl)-2-bromoethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl and nonafluorobutylsulfonyl;

C 3 -C 6 -alkenyloxy: for example prop-1-en-1-yloxy, prop-2-en-1-yloxy, 1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, penten-1-yloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yloxy, 1-methylbut-1-en-1-yloxy, 2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy, 1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, hex-1-en-1-yloxy, hex-2-en-1-yloxy, hex-3-en-1-yloxy, hex-4-en-1-yloxy, hex-5-en-1-yloxy, 1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-en-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy; 1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy and 1-ethyl-2-methylprop-2-en-1-yloxy;

›C 3 -C 6 -alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl…

C 3 -C 6 -alkenyl: prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methylbut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, hex-1-en-1-yl, hex-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut-1-en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-1-en-1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-yl, 1-ethyl-1-methylprop-2-en-1-yl, 1-ethyl-2-methylprop-1-en-1-yl and 1-ethyl-2-methylprop-2-en-1-yl.

The term “cyclic ring system having 3 to 14 ring atoms” denotes: C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, a bi- or tricyclic carbocyclic or heterocyclic ring system having up to 14 ring atoms, where the ring system may be saturated or contain one, two or three double bonds and, in the case of the heterocyclic rings, may contain one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. The “cyclic ring systems having 3 to 14 ring atoms” may be partially or fully halogenated and/or may carry one to three of the following groups:

C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy.

Examples of other meanings are:

C 3 -C 6 -cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

C 3 -C 8 -cycloalkyl: C 3 -C 6 -cycloalkyl as mentioned above, and also cycloheptyl or cyclooctyl;

C 5 -C 6 -cycloalkenyl: cyclopentenyl or cyclohexenyl;

C 3 -C 6 -cycloalkenyl: C 5 -C 6 -cycloalkenyl as mentioned above, and also cyclopropenyl or cyclobutenyl;

C 3 -C 8 -cycloalkenyl: C 3 -C 6 -cycloalkenyl as mentioned above, and also cycloheptenyl or cyclooctenyl;

bi- or tricyclic ring system: for example adamantyl, norbornyl, camphyl, camphenyl or norbornenyl.

The phenyl rings are preferably unsubstituted or carry one to three halogen atoms and/or one nitro group, one cyano group, one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy groups.

Emphasis is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables both on their own and in combination with one another have the following meanings:

X is O, NR 6 or CR 7 R 8 ;

Y is O, S, NR 9 or CR 10 R 11 ;

R 1 is nitro, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, C 1 -C 4 -alkyl, such as methyl or ethyl, or C 1 -C 4 -alkoxy, such as methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R 2 ,R 3 ,R 7 ,R 8 ,R 10 ,R 11 are hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; particularly preferably hydrogen, methyl, ethyl, propyl, 1-methylethyl, fluoromethyl or chloromethyl; with very particular preference hydrogen, methyl, ethyl or chloromethyl;

or

R 3 and R 6 or R 3 and R 8 or R 3 and R 9 or R 3 and R 11 together form a bond;

R 4 is halogen, nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C 1 -C 2 -haloalkyl, such as difluoromethyl or trifluoromethyl, C 1 -C 2 -alkoxy, such as methoxy or ethoxy, C 1 -C 2 -haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C 1 -C 3 -alkylthio, such as methylthio, ethylthio or 1-methyl-1-ethylthio, or C 1 -C 3 -alkylsulfonyl, such as methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;

R 5 is hydrogen, halogen or methyl or ethyl; particularly preferably hydrogen, chlorine or methyl; with very particular preference hydrogen;

R 6 , R 9 are hydrogen or C 1 -C 4 -alkyl; particularly preferably hydrogen, methyl or ethyl; with very particular preference methyl;

R 12 is hydroxyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl, C 1 -C 4 -alkoxy, C 3 -C 6 -alkenyloxy, C 1 -C 4 -alkylsulfonyloxy, C 1 -C 4 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy;

R 13 is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl, a bi- or tricyclic carbocyclic or heterocyclic ring system having up to 14 ring atoms, where the ring system may be saturated or contain one, two or three double bonds and, in the case of the heterocyclic rings, may contain one to three heteroatoms selected from the group consisting of oxygen, nitrogen and sulfur. The “cyclic ring systems having 3 to 14 ring atoms” may be partially or fully halogenated and/or may carry one to three of the following groups: C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy;

›particularly preferably C 3 -C 8 -cycloalkyl, C…

particularly preferably C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or a bi- or tricyclic carbocyclic ring system which contains up to 14 ring atoms and is saturated or contains one, two or three double bonds, and where the radicals mentioned may be partially or fully halogenated and/or may carry one to three of the following groups: C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy; with very particular preference C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl or norbornenyl; more preferably C 3 -C 6 -cycloalkyl; with most preference cyclopropyl;

R 14 is hydrogen or C 1 -C 4 -alkyl; particularly preferably hydrogen or methyl.

Preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where:

X is O;

R 1 is nitro, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R 4 is halogen, nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C 1 -C 2 -haloalkyl, such as difluoromethyl or trifluoromethyl, C 1 -C 2 -alkoxy, C 1 -C 2 -haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C 1 -C 2 -alkylthio, such as methylthio or ethylthio, or C 1 -C 2 -alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.

Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR 10 R 11 ;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R 2 ,R 3 ,R 10 ,R 11 are hydrogen, C 1 -C 4 -alkyl; or R 3 and R 11 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R 3 and R 11 together form a bond;

R 4 is nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably nitro, C 1 -C 2 -haloalkyl, such as difluoromethyl or trifluoromethyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkoxy, such as difluoromethoxy;

R 5 is hydrogen;

R 12 is hydroxyl, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl;

R 13 is C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C 3 -C 6 -cycloalkyl; with very particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR 10 R 11 ;

R 2 ,R 3 ,R 10 ,R 11 are hydrogen or methyl or ethyl; preferably hydrogen or methyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR 10 R 11 ;

R 2 ,R 10 are hydrogen or methyl or ethyl; preferably hydrogen or methyl;

R 3 and R 11 together form a bond.

Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR 10 R 11 ;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R 2 ,R 3 ,R 10 ,R 11 are hydrogen or C 1 -C 4 -alkyl; or R 3 and R 11 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R 3 and R 11 together form a bond;

R 4 is halogen, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;

R 5 is hydrogen;

R 12 is hydroxyl, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl;

R 13 is C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl or a bi- or tricyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C 3 -C 6 -cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR 10 R 11 ;

R 2 ,R 3 ,R 10 ,R 11 are hydrogen or methyl or ethyl; preferably hydrogen or methyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is O;

Y is CR 10 R 11 ;

R 2 ,R 10 are hydrogen or methyl or ethyl; preferably hydrogen or methyl;

R 3 and R 11 together form a bond.

Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:

X is NR 6 ;

R 1 is nitro, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R 4 is halogen, nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C 1 -C 2 -haloalkyl, such as difluoromethyl or trifluoromethyl, C 1 -C 2 -alkoxy, such as methoxy or ethoxy, C 1 -C 2 -haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C 1 -C 2 -alkylthio, such as methylthio or ethylthio, or C 1 -C 2 -alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.

›Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives…

Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N(C 1 -C 6 -alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is NR 9 or CR 10 R 11 ;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R 2 ,R 3 ,R 10 ,R 11 are hydrogen or C 1 -C 4 -alkyl; or R 3 and R 9 or R 3 and R 11 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R 3 and R 9 or R 3 and R 11 together form a bond;

R 4 is nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably nitro, C 1 -C 2 -haloalkyl, such as difluoromethyl or trifluoromethyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkoxy, such as difluoromethoxy;

R 5 is hydrogen;

R 9 is hydrogen or C 1 -C 4 -alkyl; particularly preferably C 1 -C 4 -alkyl; with particular preference methyl or ethyl;

R 12 is hydroxyl, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl;

R 13 is C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C 3 -C 6 -cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C 1 -C 6 -alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is CR 10 R 11 ;

R 2 ,R 3 ,R 10 ,R 11 are hydrogen or C 1 -C 4 -alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C 1 -C 6 -alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is NR 9 or CR 10 R 11 ;

R 2 ,R 10 are hydrogen or C 1 -C 4 -alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;

R 3 and R 9 or R 3 and R 11 together form a bond.

Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C 1 -C 6 -alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is NR 9 or CR 10 R 11 ;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R 2 ,R 3 ,R 10 ,R 11 are hydrogen or C 1 -C 4 -alkyl; or R 3 and R 9 or R 3 and R 11 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R 3 and R 9 or R 3 and R 11 together form a bond;

R 4 is halogen, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;

R 5 is hydrogen;

R 9 is hydrogen or C 1 -C 4 -alkyl; particularly preferably C 1 -C 4 -alkyl; with particular preference methyl or ethyl;

R 12 is hydroxyl, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl;

R 13 is C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl or a bi- or tricyclic carbocyclic ring system, selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C 1 -C 6 -cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C 1 -C 6 -alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is CR 10 R 11 ;

R 2 ,R 3 ,R 10 ,R 11 are hydrogen or C 1 -C 4 -alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is N-(C 1 -C 6 -alkyl); particularly preferably N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

Y is NR 9 or CR 10 R 11 ;

R 2 ,R 10 are hydrogen or C 1 -C 4 -alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;

R 3 and R 9 or R 3 and R 11 together form a bond.

Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is NR 6 ;

Y is O, S or N-(C 1 -C 6 -alkyl); particularly preferably O, S or N-methyl, N-ethyl, N-(1-methyl-1-ethyl) or N-propyl;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R 2 is hydrogen or C 1 -C 4 -alkyl; particularly preferably hydrogen, methyl or ethyl;

R 3 and R 6 together form a bond;

R 5 is hydrogen;

R 12 is hydroxyl, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl;

R 13 is C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C 3 -C 6 -cycloalkyl; with particular preference cyclopropyl.

›Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives…

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

R 4 is nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably nitro, C 1 -C 2 -haloalkyl, such as difluoromethyl or trifluoromethyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkoxy, such as difluoromethoxy.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

R 4 is halogen, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl.

Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where:

X is CR 7 R 8 ;

R 1 is nitro, halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; with particular preference halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with very particular preference chlorine, methyl or methoxy;

R 4 is halogen, nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl; particularly preferably halogen, such as chlorine or bromine, nitro, C 1 -C 2 -haloalkyl, such as difluoromethyl or trifluoromethyl, C 1 -C 2 -alkoxy, such as methoxy or ethoxy, C 1 -C 2 -haloalkoxy, such as difluoromethoxy, chlorodifluoromethoxy or trifluoromethoxy, C 1 -C 2 -alkylthio, such as methylthio or ethylthio, or C 1 -C 2 -alkylsulfonyl, such as methylsulfonyl or ethylsulfonyl.

Particular preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR 7 R 8 ;

Y is O, S or NR 9 ;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl, methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R 2 ,R 3 ,R 7 ,R 8 are hydrogen or C 1 -C 4 -alkyl; or R 3 and R 8 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R 3 and R 8 together form a bond;

R 4 is nitro, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably nitro, C 1 -C 2 -haloalkyl, such as difluoromethyl or trifluoromethyl, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkoxy, such as difluoromethyloxy;

R 5 is hydrogen;

R 9 is hydrogen or C 1 -C 4 -alkyl; particularly preferably C 1 -C 4 -alkyl;

R 12 is hydroxyl, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl;

R 13 is C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl or a bi or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C 3 -C 6 -cycloalkyl; with particular preference cyclopropyl.

Most preference is given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR 7 R 8 ;

Y is O, S or NR 9 ;

R 2 ,R 3 ,R 7 ,R 8 are hydrogen or C 1 -C 4 -alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;

R 9 is hydrogen or C 1 -C 4 -alkyl; preferably C 1 -C 4 -alkyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR 7 R 8 ;

Y is O, S or NR 9 ;

R 2 ,R 7 are hydrogen or C 1 -C 4 -alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;

R 3 and R 8 together form a bond;

R 9 is hydrogen or C 1 -C 4 -alkyl; preferably C 1 -C 4 -alkyl.

Especially preferred in this case are the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where Y is S.

Particular preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR 7 R 8 ;

Y is O, S or NR 9 ;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably halogen, such as fluorine, chlorine or bromine, methyl or ethyl or methoxy or ethoxy; with particular preference chlorine, methyl or methoxy;

R 2 ,R 3 ,R 7 ,R 8 are hydrogen or C 1 -C 4 -alkyl; or R 3 and R 8 together form a bond; particularly preferably hydrogen, methyl or ethyl; or R 3 and R 8 together form a bond;

R 4 is halogen, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulfonyl; particularly preferably chlorine or bromine, methylthio, ethylthio or 1-methyl-1-ethylthio or methylsulfonyl, ethylsulfonyl, 1-methylethylsulfonyl or propylsulfonyl;

R 5 is hydrogen;

R 9 is hydrogen or C 1 -C 4 -alkyl; particularly preferably C 1 -C 4 -alkyl; with particular preference methyl or ethyl;

R 12 is hydroxyl, C 1 -C 6 -alkylsulfonyloxy, C 1 -C 6 -alkylcarbonyloxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl;

R 13 is C 3 -C 6 -cycloalkyl, C 5 -C 6 -cycloalkenyl or a bi- or tricyclic carbocyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl and norbornenyl; particularly preferably C 3 -C 6 -cycloalkyl; with particular preference cyclopropyl.

Preference is furthermore given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR 7 R 8 ;

Y is O, S or NR 9 ;

R 2 ,R 3 ,R 7 ,R 8 are hydrogen or C 1 -C 4 -alkyl; preferably hydrogen, methyl or ethyl; particularly preferably hydrogen or methyl;

R 9 is hydrogen or C 1 -C 4 -alkyl; preferably C 1 -C 4 -alkyl.

Most preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where

X is CR 7 R 8 ;

Y is O, S or NR 9 ;

R 2 ,R 7 are hydrogen or C 1 -C 4 -alkyl; preferably hydrogen, methyl or ethyl; with particular preference hydrogen or methyl;

›R 3 and R 8 together form a…

R 3 and R 8 together form a bond;

R 9 is hydrogen or C 1 -C 4 -alkyl; preferably C 1 -C 4 -alkyl.

Especially preferred in this case are the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where Y is S.

Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:

X is O;

Y is CR 10 R 11 ;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; particularly preferably chlorine, methyl or methoxy; also particularly preferably halogen or C 1 -C 4 -alkyl; with particular preference chlorine or methyl;

R 1 ,R 3 ,R 10 ,R 11 are hydrogen;

R 4 is C 1 -C 4 -alkylsulfonyl; particularly preferably methylsulfonyl;

R 5 is hydrogen;

R 12 is hydroxyl, C 1 -C 6 -alkoxy, phenylsulfonyloxy or phenylcarbonyloxy, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; particularly preferably hydroxyl, C 1 -C 6 -alkoxy or phenylcarbonyloxy, where the phenyl radical may be partially or fully halogenated and/or may carry one to three of the following groups; nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy;

R 13 is C 3 -C 6 -cycloalkyl or a bi- or tricyclic ring system selected from the group consisting of: adamantyl, norbornyl, camphyl, camphenyl or norbornenyl; particularly preferably cyclopropyl, cyclopentyl, 2-norbornyl or 2-adamantyl; with particular preference cyclopentyl or 2-norbornyl; also with particular preference cyclopropyl;

R 14 is hydrogen;

Preference is also given to the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I where the variables have the following meanings:

X is O;

Y is CR 10 R 11 ;

R 1 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy;

R 4 is C 1 -C 4 -alkylsulfonyl;

R 13 is C 3 -C 6 -cycloalkyl.

Most particularly preferred are the compounds of the formula Ia1 (=I where R 1 =Cl; R 13 =cyclo-C 3 H 5 and R 5 and R 14 =H), in particular the compounds Ia1.1 to Ta1.765 of Table 1, where the radical definitions X, Y and R 1 to R 14 are of particular importance for the compounds according to the invention not only in combination with one another but also in each case on their own.

Most particular preference is also given to the compounds of the formula Ia2, in particular to the compounds Ia2.1, to Ia2.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia3, in particular to the compounds Ia3.1 to Ia3.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 13 is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ia4, in particular to the compounds Ia4.1 to Ia4.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 13 is cyclopentyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia5, in particular to the compounds Ia5.1 to Ia5.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ia6, in particular to the compounds Ia6.1 to Ia6.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 13 is cyclohexyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia7, in particular to the compounds Ia7.1 to Ia7.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ia8, in particular to the compounds Ia8.1 to Ia8.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 13 is 2-norbornyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia9, in particular to the compounds Ia9.1 to Ia9.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ia10, in particular to the compounds Ia10.1 to Ia10.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 13 is 2-adamantyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia11, in particular to the compounds Ia11.1 to Ia11.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R 1 is methyl.

Most particular preference is also given to the compounds of the formula Ia12, in particular to the compounds Ia12.1 to Ia12.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R 1 is methyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia13, in particular to the compounds Ia13.1 to Ia13.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methyl and R 13 is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ia14, in particular to the compounds Ia14.1 to Ia14.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methyl, R 13 is cyclopentyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia15, in particular to the compounds Ia15.1 to Ia15.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methyl and R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ia16, in particular to the compounds Ia16.1 to Ia16.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methyl, R 13 is cyclohexyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia17, in particular to the compounds Ia17.1 to Ia17.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methyl and R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ia18, in particular to the compounds Ia18.1 to Ia18.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methyl, R 12 is 2-norbornyl and R 14 is methyl.

›Most particular preference is also given to the…

Most particular preference is also given to the compounds of the formula Ia19, in particular to the compounds Ia19.1 to Ia19.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methyl and R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ia20, in particular to the compounds Ia20.1 to Ia20.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methyl, R 13 is 2-adamantyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia21, in particular to the compounds Ia21.1 to Ia21.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R 1 is methoxy.

Most particular preference is also given to the compounds of the formula Ia22, in particular to the compounds Ia22.1 to Ia22.765 which differ from the corresponding compounds Ia1.1 to Ia1.765 in that R 1 is methoxy and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia23, in particular to the compounds Ia23.1 to Ia23.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methoxy and R 13 is cyclopentyl.

Most particuiar preference is also given to the compounds of the formula Ia24, in particular to the compounds Ia24.1 to Ia24.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methoxy, R 13 is cyclopentyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia25, in particular to the compounds Ia25.1 to Ia25.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methoxy and R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ia26, in particular to the compounds Ia26.1 to Ia26.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methoxy, R 13 is cyclohexyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia27, in particular to the compounds Ia27.1 to Ia27.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methoxy and R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ia28, in particular to the compounds Ia28.1 to Ia28.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methoxy, R 13 is norbornyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ia29, in particular to the compounds Ia29.1 to Ia29.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methoxy and R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ia30, in particular to the compounds Ia30.1 to Ia30.765 which differ from the compounds Ia1.1 to Ia1.765 in that R 1 is methoxy, R 13 is 2-adamantyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib1 (=I where R 1 =Cl, R 3 and R 9 or R 3 and R 11 together form a bond, R 13 =cyclo-C 3 H 5 and R 5 and R 14 =H), in particular to the compounds Ib1.1 to Ib1.420 of Table 2 where the radical definitions X, Y and R 1 to R 14 are of particular importance for the compounds according to the invention not only in combination with one another but also in each case on their own.

Most particular preference is also given to the compounds of the formula Ib2, in particular to the compounds Ib2.1 to Ib2.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib3, in particular to the compounds Ib3.1 to Ib3.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 13 is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ib4, in particular to the compounds Ib4.1 to Ib4.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 13 is cyclopentyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib5, in particular to the compounds Ib5.1 to Ib5.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ib6, in particular to the compounds Ib6.1 to Ib6.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 13 is cyclohexyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib7, in particular to the compounds Ib7.1 to Ib7.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ib8, in particular to the compounds Ib8.1 to Ib8.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 13 is 2-norbornyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib9, in particular to the compounds Ib9.1 to Ib9.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ib10, in particular to the compounds Ib10.1 to Ib10.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 13 is 2-adamantyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib11, in particular to the compounds Ib11.1 to Ib11.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R 1 is methyl.

Most particular preference is also given to the compounds of the formula Ib12, in particular to the compounds Ib12.1 to Ib12.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R 1 is methyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib13, in particular to the compounds Ib13.1 to Ib13.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methyl and R 13 is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ib14, in particular to the compounds Ib14.1 to Ib14.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methyl, R 13 is cyclopentyl and R 14 is methyl.

›Most particular preference is also given to the…

Most particular preference is also given to the compounds of the formula Ib15, in particular to the compounds Ib15.1 to Ib15.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methyl and R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ib16, in particular to the compounds Ib16.1 to Ib16.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methyl, R 13 is cyclohexyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib17, in particular to the compounds Ib17.1 to Ib17.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methyl and R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ib18, in particular to the compounds Ib18.1 to Ib18.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methyl, R 13 is 2-norbornyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib19, in particular to the compounds Ib19.1 to Ib19.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methyl and R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ib20, in particular to the compounds Ib20.1 to Ib20.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methyl, R 13 is 2-adamantyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib21, in particular to the compounds Ib21.1 to Ib21.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R 1 is methoxy.

Most particular preference is also given to the compounds of the formula Ib22, in particular to the compounds Ib22.1 to Ib22.420 which differ from the corresponding compounds Ib1.1 to Ib1.420 in that R 1 is methoxy and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib23, in particular to the compounds Ib23.1 to Ib23.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methoxy and R 13 is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ib24, in particular to the compounds Ib24.1 to Ib24.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methoxy, R 13 is cyclopentyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib25, in particular to the compounds Ib25.1 to Ib25.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methoxy and R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ib26, in particular to the compounds Ib26.1 to Ib26.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methoxy, R 13 is cyclohexyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib27, in particular to the compounds Ib27.1 to Ib27.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methoxy and R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ib28, in particular to the compounds Ib28.1 to Ib28.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methoxy, R 13 is 2-norbornyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ib29, in particular to the compounds Ib29.1 to Ib29.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methoxy and R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ib30, in particular to the compounds Ib30.1 to Ib30.420 which differ from the compounds Ib1.1 to Ib1.420 in that R 1 is methoxy, R 13 is 2-adamantyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic1 (=I where R 1 =Cl, R 3 and R 6 or R 3 and R 8 together form a bond, R 13 =cyclo-C 3 H 5 and R 5 and R 14 =H), in particular to the compounds Ic1.1-Ic1.720 of Table 3, where the radical definitions are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own.

Most particular preference is also given to the compounds of the formula Ic2, in particular to the compounds Ic2.1 to Ic2.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic3, in particular to the compounds Ic3.1 to Ic3.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 13 is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ic4, in particular to the compounds Ic4.1 to Ic4.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 13 is cyclopentyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic5, in particular to the compounds Ic5.1 to Ic5.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ic6, in particular to the compounds Ic6.1 to Ic6.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 13 is cyclohexyl and R 14 is Methyl.

Most particular preference is also given to the compounds of the formula Ic7, in particular to the compounds Ic7.1 to Ic7.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ic8, in particular to the compounds Ic8.1 to Ic8.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 13 is 2-norbornyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic9, in particular to the compounds Ic9.1 to Ic9.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ic10, in particular to the compounds Ic10.1 to Ic10.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 13 is 2-adamantyl and R 14 is methyl.

›Most particular preference is also given to the…

Most particular preference is also given to the compounds of the formula Ic11, in particular to the compounds Ic11.1 to Ic11.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R 1 is methyl.

Most particular preference is also given to the compounds of the formula Ic12, in particular to the compounds Ic12.1 to Ic12.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R 1 is methyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic13, in particular to the compounds Ic13.1 to Ic13.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methyl and R 13 is cyclopentyl.

Most particular preference is also given to the compounds of the formula Ic14, in particular to the compounds Ic14.1 to Ic14.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methyl, R 13 is cyclopentyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic15, in particular to the compounds Ic15.1 to Ic15.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methyl and R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ic16, in particular to the compounds Ic16.1 to Ic16.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methyl, R 13 is cyclohexyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic17, in particular to the compounds Ic17.1 to Ic17.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methyl and R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ic18, in particular to the compounds Ic18.1 to Ic18.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methyl, R 13 is 2-norbornyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic19, in particular to the compounds Ic19.1 to Ic19.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methyl and R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ic20, in particular to the compounds Ic20.1 to Ic20.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methyl, R 13 is 2-adamantyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic21, in particular to the compounds Ic21.1 to Ic21.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R 1 is methoxy.

Most particular preference is also given to the compounds of the formula Ic22, in particular to the compounds Ic22.1 to Ic22.720 which differ from the corresponding compounds Ic1.1 to Ic1.720 in that R 1 is methoxy and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic23, in particular to the compounds Ic23.1 to Ic23.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methoxy and R 13 is cyclopentyl.

Most particular preferenceis also given to the compounds of the formula Ic24, in particular to the compounds Ic24.1 to Ic24.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methoxy, R 13 is cyclopentyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic25, in particular to the compounds Ic25.1 to Ic25.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methoxy and R 13 is cyclohexyl.

Most particular preference is also given to the compounds of the formula Ic26, in particular to the compounds Ic26.1 to Ic26.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methoxy, R 13 is cyclohexyl and R 14 is methyl.

Most particular preference is also given to the compounds of the formula Ic27, in particular to the compounds Ic27.1 to Ic27.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methoxy and R 13 is 2-norbornyl.

Most particular preference is also given to the compounds of the formula Ic28, in particular to the compounds Ic28.1 to Ic28.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methoxy, R 13 is 2-norbornyl and R 14 is methyl.

Most particular preference is Also given to the compounds of the formula Ic29, in particular to the compounds Ic29.1 to Ic29.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methoxy and R 13 is 2-adamantyl.

Most particular preference is also given to the compounds of the formula Ic30, in particular to the compounds Ic30.1 to Ic30.720 which differ from the compounds Ic1.1 to Ic1.720 in that R 1 is methoxy, R 13 is 2-adamantyl and R 14 is methyl.

The 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I can be obtained by various routes, for example by the processes below.

Process A

Reaction of pyrazoles of the formula II with an activated benzoic acid IIIα or a benzoic acid IIIβ, which is preferably activated in situ, to give the corresponding acylation product IV, followed by rearrangement, gives compounds of the formula I where R 12 =OH.

L 1 is a nucleophilically displaceable leaving group, such as halogen, for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, etc.

The activated benzoic acid can be employed directly, such as in the case of the benzoyl halides, or be generated in situ, for example using dicyclohexylcarbodiimide, triphenylphosphine/azodicarboxylic ester, 2-pyridine disulfide/triphenylphosphine, carbonyldiimidazole, etc.

It may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are advantageously employed in this case in equimolar amounts. A slight excess of auxiliary base, for example from 1.2 to 1.5 molar equivalents, based on II, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, pyridine or alkali metal carbonates. Suitable for use as solvents are, for example, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, such as toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, dimethoxyethane, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

›If the activated carboxylic acid component used is…

If the activated carboxylic acid component used is a benzoyl halide, it may be advantageous to cool the reaction mixture to 0-10° C. when adding this reaction partner. The mixture is subsequently stirred at 20-100° C., preferably at 25-50° C., until the reaction has ended. work-up is carried out in a customary manner, for example by pouring the reaction mixture into water and extracting the product of value. Solvents which are particularly suitable for this purpose are methylene chloride, diethyl ether, dimethoxyethane and ethyl acetate. The organic phase is dried and the solvent is removed, after which the crude ester can be employed for the rearrangement without any further purification.

The rearrangement of the esters to the compounds of the formula I is advantageously carried out at 20-40° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as catalyst.

Suitable solvents are, for example, acetonitrile, methylene chloride, 1,2-dichlorcethane, dioxane, ethyl acetate, dimethoxyethane, toluene or mixtures of these. Preferred solvents are acetonitrile and dioxane.

Suitable bases are tertiary amines, such as triethylamine or pyridine, or alkali metal carbonates, such as sodium carbonate or potassium carbonate, which are preferably employed in an equimolar amount or an up to four-fold excess, based on the ester. Preference is given to using triethylamine or alkali metal carbonates, preferably in twice the equimolar amount, based on the ester.

Suitable cyano compounds are inorganic cyanides, such as sodium cyanide and potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin and trimethylsilyl cyanide. They are employed in an amount of from 1 to 50 mol percent, based on the ester. Preference is given to using acetone cyanohydrin or trimethylsilyl cyanide, for example in an amount of from 5 to 15, preferably 10, mol percent, based on the ester.

Work-up can be carried out in the manner known per se. The reaction mixture is, for example, acidified with dilute mineral acid, such as 5% strength hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can be extracted with 5-10% strength alkali metal carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the resulting precipitate is filtered off with suction and/or extracted with methylene chloride or ethyl acetate, and the mixture is dried and concentrated. (Examples for the preparation of esters of hydroxypyrazoles and for the rearrangement of the esters are given, for example, in EP-A 282 944 and U.S. Pat. No. 4,643,757).

However, it is also possible to generate the “acylation product” IV in situ by reacting a pyrazole of the formula II, or an alkali metal salt thereof with a 3-(heterocyclyl)benzene derivative of the formula V in the presence of carbon monoxide, a catalyst and a base.

L 2 is a leaving group, such as halogen, for example chlorine, bromine or iodine, or sulfonate, such as mesylate or triflate; preference is given to bromine or triflate.

The “acylation product” IV proceeds to react, directly or indirectly, to give the 1-cycloalkylpyrazolylbenzoyl derivative of the formula I.

Suitable catalysts are palladium-ligand complexes in which the palladium is present in oxidation state 0, metallic palladium, which has optionally been absorbed on a carrier, and preferably palladium(II) salts. The reaction with palladium(II) salts and metallic palladium is preferably carried out in the presence of complex ligands.

An example of a suitable palladium(0)-ligand complex is tetrakis(triphenylphosphine)palladium.

Metallic palladium is preferably absorbed on an inert carrier such as, for example, activated carbon, silica, alumina, barium sulfate or calcium carbonate. The reaction is preferably carried out in the presence of complex ligands such as, for example; triphenylphosphine.

Examples of suitable palladium(II) salts are palladium acetate and palladium chloride. The presence of complex ligands such as, for example, triphenylphosphine is preferred.

Suitable complex ligands for the palladium-ligand complexes, or in whose presence the reaction is preferably carried out with metallic palladium or palladium(II) salts, are tertiary phosphines whose structure is represented by the following formulae:

where z is 1 to 4 and the radicals R a to R g are C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, aryl-C 1 -C 2 -alkyl or, preferably, aryl. Aryl is, for example, naphthyl and unsubstituted or substituted phenyl such as, for example, 2-tolyl and, in particular, unsubstituted phenyl.

The complex palladium salts can be prepared in a manner known per se starting from commercially available palladium salts such as palladium chloride or palladium acetate and the appropriate phosphines such as, for example, triphenylphosphine or 1,2-bis(diphenylphosphino)ethane. Many of the complexed palladium salts are commercially available. Preferred palladium salts are [(R)(+)2,2′-bis(diphenylphosphino)-1,1′-binaphthyl]palladium(II) chloride, bis(triphenylphosphine)palladium(II) acetate and, in particular, bis(triphenylphosphine)palladium(II) chloride.

The palladium catalyst is usually employed in a concentration of from 0.05 to 5 mol %, and preferably 1-3 mol %.

Suitable bases are tertiary amines, such as, for example, N-methylpiperidine, ethyldiisopropylamine, 1,8-bisdimethylaminonaphthalene or, in particular, triethylamine. Also suitable is alkali metal carbonate, such as sodium carbonate or potassium carbonate. However, mixtures of potassium carbonate and triethylamine are also suitable.

In general, from 2 to 4 molar equivalents, in particular 2 molar equivalents, of the alkali metal carbonate, and from 1 to 4 molar equivalents, in particular 2 molar equivalents, of the tertiary amine are employed, based on the 3-(heterocylyl)benzene derivative of the formula V.

Suitable solvents are nitriles, such as benzonitrile and acetonitrile, amides, such as dimethylformide, dimethylacetamide, tetra-C 1 -C 4 -alkylureas or N-methylpyrrolidone and, preferably, ethers, such as tetrahydrofuran and methyl tert-butyl ethers. Particular preference is given to ethers, such as 1,4-dioxane and dimethoxyethane.

›Process B Compounds of the formula I where…

Process B

Compounds of the formula I where R 12 =hydroxyl are obtained by reacting compounds of the formula I where R 12 =hydroxyl with alkylating agents, sulfonylating agents or acylating agents L 3 -R 12a (VI)

L 3 is a nucleophilically displaceable leaving group, such as halogen, for example bromine or chlorine, acyloxy, for example acetyloxy or ethylcarbonyloxy, or alkylsulfonyloxy, for example methylsulfonyloxy or trifluoromethylsulfonyloxy.

R 12a is C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbonyl, phenylsulfonyl or phenylcarbonyl, where the phenyl radical of the two last-mentioned substituents may be partially or fully halogenated and/or may carry one to three of the following groups: nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy.

The compounds of the formula VI can be employed directly, such as, for example, in the case of the sulfonyl halides or sulfonic anhydrides, or be generated in situ, for example activated sulfonic acids (using sulfonic acid and dicyclohexylcarbonyldiimide, carbonyldiimidazole, etc.).

The starting materials are generally employed in equimolar amounts. However, it may also be advantageous to employ an excess of one or the other component.

If appropriate, it may be advantageous to carry out the reaction in the presence of a base. The reactants and the auxiliary base are advantageously employed in equimolar amounts. An excess of auxiliary base, for example from 1.5 to 3 molar equivalents, based on I, may be advantageous in certain cases.

Suitable auxiliary bases are tertiary alkylamines, such as triethylamine, pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, and alkali metal hydrides, for example sodium hydride. Preference is given to using triethylamine and pyridine.

Suitable solvents are, for example, chlorinated hydrocarbons, such as methylene chloride and 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran and dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide, or esters, such as ethyl acetate, or mixtures of these.

In general, the reaction temperature is in the range from 0° C. to the boiling point of the reaction mixture.

Work-up can be carried out in the manner known per se to give the product.

The pyrazoles of the formula II used as starting materials are known or can be prepared by processes known per se (for example EP-A 240 001 and J. Prakt. Chem. 315, 383 (1973)). The activated benzoic acids IIIα and the benzoic acids IIIβ are likewise known or can be prepared in the manner known per se (for example WO 96/26206). Furthermore, the 3-(heterocyclyl)benzene derivatives of the formula V are known or can be prepared in the manner known per se (PCT/EP/99/03006).

›PREPARATION EXAMPLE · 1 of 3

4-[2-Methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-cyclopentyl-5-hydroxy-1H-pyrazole (compound 4.6)

1.9 g (9.4 mmol) of dicyclohexylcarbodiimide and 1.3 g (8.8 mmol) of 1-cyclopentyl-5-hydroxy-1H-pyrazole were added to a solution of 2.5 g (8.8 mmol) of 2-methyl-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid in 100 ml of dioxane, and the mixture was stirred at room temperature for 12 hours. Solid components were then filtered off and the filtrate was admixed with 1.5 g (10 mmol) of potassium carbonate and refluxed for 4 hours. The solvent was removed, the residue was then taken up in water and the mixture was washed with ethyl acetate, and then adjusted to pH 3 using 10% strength hydrochloric acid and extracted with methylene chloride. The solvent of the resulting organic phase was distilled off, the residue was taken up in 300 ml of aqueous potassium carbonate solution, insoluble components were filtered off, the pH was adjusted to 3 using 10% strength hydrochloric acid and the resulting precipitate was separated off and dried. Yield: 1.5 g (42% of theory) of 4-[2-methyl-3-(4,5-dihydro-isoxazol-3-yl)-4-methylsulfonylbenzoyl]-1-cyclopentyl-5-hydroxy-1H-pyrazole

M.p.: 135-140° C.

In addition to the compound above, Table 4 lists other 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I which were prepared or are preparable in a similar manner;

The 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising compounds of the formula I control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method used, the compounds of the formula I, or the herbicidal. compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica ( Coffea canephora, Coffea liberica ), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, ( Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium ), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum ( N. rustica ), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor ( S. vulgare ), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds of the formula I may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.

The compounds of the formula I, or the herbicidal compositions comprising them, can be used for example in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly-concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should ensure the finest distribution possible of the active compounds according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customarily used for formulating of crop protection agents.

Essentially, suitable inert auxiliaries include: mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the substances, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates comprising active compound, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

Suitable surfactants (adjuvants) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g. ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ether, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol asters, lignin-sulfite waste liquors or methylcellulose.

›PREPARATION EXAMPLE · 2 of 3

Powders, materials for broadcasting and dusting agents can be prepared by mixing or grinding the active compounds together with a solid carrier.

Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise about from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

The following formulation examples illustrate the preparation of such formulations:

I. 20 parts by weight of compound No. 4.6 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of calcium dodecylbenzenesulfonate and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

II. 20 parts by weight of compound no. 4.6 are dissolved in a mixture composed of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

III. 20 parts by weight of compound No. 4.6 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280° C. and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.

IV. 20 parts by weight of compound No. 4.6 are mixed thoroughly with 3 parts by weight of sodium diisobutylnaphthalenesulfonate, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel, and the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1% by weight of the active compound.

V. 3 parts by weight of compound No. 4.6 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3% by weight of the active compound.

VI. 20 parts by weight of compound No. 4.6 are mixed intimately with 2 parts by weight of calcium dodecylbenzenesulfonate, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.

VII. 1 part by weight of compound No. 4.6 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, 20 parts by weight of etboxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a stable emulsion concentrate.

VIII. 1 part by weight of compound No. 4.6 of the formula I is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (=nonionic emulsifier based on ethoxylated castor oil).

This gives a stable emulsion concentrate.

The compounds of the formula I or the herbicidal compositions can be applied pre- or post-emergence. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

The application rates of compound of the formula I are from 0.001 to 3.0, preferably 0.01 to 1.0 kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.

To widen the activity spectrum and to achieve synergistic effects, the 1-cycloalkylpyrazolylbenzoyl derivatives of the formula I may be mixed with a large number of representatives of other herbicidal or growth-regulating active compound groups and applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-((het)aroyl)-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF 3 -phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexeneone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and hetaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.

›PREPARATION EXAMPLE · 3 of 3

It may furthermore be advantageous to apply the compounds of the formula I, alone or else concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates may also be added.

Use Examples

The herbicidal activity of the 1-cycloalkylpyrazolyl benzoyl derivatives of the formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover causes uniform germination of the test plants, unless this is adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The application rate for the post-emergence treatment was 0.5 or 0.25 kg of a.s. (active substance)/ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

The evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial parts and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were of the following species:

Scientific name

Common name

Brachiaria plantaginea

alexander grass

Chenopodium album

lamb's-quarters

Echinochloa crus-galli

barnyard grass

Polygonum persicaria

lady's-thumb

At application rates of 0.5 or 0.25 kg/ha, the compound 4.6 (Table 4) showed very good post-emergence action against the abovementioned undesirable plants.

›Tables in the description — 4
TABLE 1
No.XR 2R 3YR 4R 12
Ia1.1OHHCH 2SCH 3OH
Ia1.2OHHCH 2SCH 2 CH 3OH
Ia1.3OHHCH 2SO 2 CH 3OH
Ia1.4OHHCH 2SO 2 CH 2 CH 3OH
Ia1.5OHHCH 2SO 2 CH(CH 3 ) 2OH
Ia1.6OHHCH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.7OHHCH 3ClOH
Ia1.8OHHCH 2BrOH
Ia1.9OHHCH 2NO 2OH
Ia1.10OHHCH 2CHF 2OH
Ia1.11OHHCH 2CF 3OH
Ia1.12OHHCH 2OCH 3OH
Ia1.13OHHCH 2OCH 2 CH 3OH
Ia1.14OHHCH 2OCHF 2OH
Ia1.15OHHCH 2OCF 3OH
Ia1.16OCH 3HCH 2SCH 3OH
Ia1.17OCH 3HCH 2SCH 2 CH 3OH
Ia1.18OCH 3HCH 2SO 2 CH 3OH
Ia1.19OCH 3HCH 2SO 2 CH 2 CH 3OH
Ia1.20OCH 3HCH 2SO 2 CH(CH 3 ) 2OH
Ia1.21OCH 3HCH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.22OCH 3HCH 2ClOH
Ia1.23OCH 3HCH 2BrOH
Ia1.24OCH 3HCH 2NO 2OH
Ia1,25OCH 3HCH 2CHF 2OH
Ia1.26OCH 3HCH 2CF 3OH
Ia1.27OCH 3HCH 2OCH 3OH
Ia1.28OCH 3HCH 2OCH 2 CH 3OH
Ia1.29OCH 3HCH 2OCHF 2OH
Ia1.30OCH 3HCH 2OCF 3OH
Ia1.31OCH 3CH 3CH 2SCH 3OH
Ia1.32OCH 3CH 3CH 2SCH 2 CH 3OH
Ia1.33OCH 3CH 3CH 2SO 2 CH 3OH
Ia1.34OCH 3CH 3CH 2SO 2 CH 2 CH 3OH
Ia1.35OCH 3CH 3CH 2SO 2 CH(CH 3 ) 2OH
Ia1.36OCH 3CH 3CH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.37OCH 3CH 3CH 2ClOH
Ia1.38OCH 3CH 3CH 2BrOH
Ia1.39OCH 3CH 3CH 2NO 2OH
Ia1.40OCH 3CH 3CH 2CHF 2OH
Ia1.41OCH 3CH 3CH 2CF 3OH
Ia1.42OCH 3CH 3CH 2OCH 3OH
Ia1.43OCH 3CH 3CH 2OCH 2 CH 3OH
Ia1.44OCH 3CH 3CH 2OCHF 2OH
Ia1.45OCH 3CH 3CH 2OCF 3OH
Ia1.46OCH 2 ClHCH 2SCH 3OH
Ia1.47OCH 2 ClHCH 2SCH 2 CH 3OH
Ia1.48OCH 2 ClHCH 2SO 2 CH 3OH
Ia1.49OCH 2 ClHCH 2SO 2 CH 2 CH 3OH
Ia1.50OCH 2 ClHCH 2SO 2 CH(CH 3 ) 2OH
Ia1.51OCH 2 ClHCH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.52OCH 2 ClHCH 2ClOH
Ia1.53OCH 2 ClHCH 2BrOH
Ia1.54OCH 2 ClHCH 2NO 2OH
Ia1.55OCH 2 ClHCH 2CHF 2OH
Ia1.56OCH 2 ClHCH 2CF 3OH
Ia1.57OCH 2 ClHCH 2OCH 3OH
Ia1.58OCH 2 ClHCH 2OCH 2 CH 3OH
Ia1.59OCH 2 ClHCH 2OCHF 2OH
Ia1.60OCH 2 ClHCH 2OCF 3OH
Ia1.61OCH 2 CH 3HCH 2SCH 3OH
Ia1.62OCH 2 CH 3HCH 2SCH 2 CH 3OH
Ia1.63OCH 2 CH 3HCH 2SO 2 CH 3OH
Ia1.64OCH 2 CH 3HCH 2SO 3 CH 2 CH 3OH
Ia1.65OCH 2 CH 3HCH 2SO 2 CH(CH 3 ) 2OH
Ia1.66OCH 2 CH 3HCH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.67OCH 2 CH 3HCH 2ClOH
Ia1.68OCH 2 CH 3HCH 2BrOH
Ia1.69OCH 2 CH 3HCH 2NO 2OH
Ia1.70OCH 2 CH 3HCH 2CHF 2OH
Ia1.71OCH 2 CH 3RCH 2CF 3OH
Ia1.72OCH 2 CH 3HCH 2OCH 3OH
Ia1.73OCH 2 CH 3HCH 2OCH 2 CH 3OH
Ia1.74OCH 2 CH 3HCH 2OCHF 2OH
Ia1.75OCH 2 CH 3HCH 2OCF 3OH
Ia1.76OCH 2 CH 3CH 2 CH 3CH 2SCH 3OH
Ia1.77OCH 2 CH 3CH 2 CH 3CH 2SCH 2 CH 3OH
Ia1.78OCH 2 CH 3CH 2 CH 3CH 2SO 2 CH 3OH
Ia1.79OCH 2 CH 3CH 2 CH 3CH 2SO 2 CH 2 CH 3OH
Ia1.80OCH 2 CH 3CH 2 CH 3CH 2SO 2 CH(CH 3 ) 2OH
Ia1.81OCH 2 CH 3CH 2 CH 3CH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.82OCH 2 CH 3CH 2 CH 3CH 2ClOH
Ia1.83OCH 2 CH 3CH 2 CH 3CH 2BrOH
Ia1.84OCH 2 CH 3CH 2 CH 3CH 2NO 2OH
Ia1.85OCH 2 CH 3CH 2 CH 3CH 2CHF 2OH
Ia1.86OCH 2 CH 3CH 2 CH 3CH 2CF 3OH
Ia1.87OCH 2 CH 3CH 2 CH 3CH 2OCH 3OH
Ia1.88OCH 2 CH 3CH 2 CH 3CH 2OCH 2 CH 3OH
Ia1.89OCH 2 CH 3CH 2 CH 3CH 2OCHF 2OH
Ia1.90OCH 2 CH 3CH 2 CH 3CH 2OCF 3OH
Ia1.91OHHCH(CH 3 )SCH 3OH
Ia1.92OHHCH(CH 3 )SCH 2 CH 3OH
Ia1.93OHHCH(CH 3 )SO 2 CH 3OH
Ia1.94OHHCH(CH 3 )SO 2 CH 2 CH 3OH
Ia1.95OHHCH(CH 3 )SO 2 CH(CH 3 ) 2OH
Ia1.96OHHCH(CH 3 )SO 2 (CH 2 ) 2 CH 3CH
Ia1.97OHHCH(CH 3 )ClOH
Ia1.98OHHCH(CH 3 )BrOH
Ia1.99OHHCH(CH 3 )NO 2OH
Ia1.100OHHCH(CH 3 )CHF 2OH
Ia1.101OHHCH(CH 3 )CF 3OH
Ia1.102OHHCH(CH 3 )OCH 3OH
Ia1.103OHHCH(CH 3 )OCH 2 CH 3OH
Ia1.104OHHCH(CH 3 )OCHF 2OH
Ia1.105OHHCH(CH 3 )OCF 3OH
Ia1.106OCH 3HCH(CH 3 )SCH 3OH
Ia1.107OCH 3HCH(CH 3 )SCH 2 CH 3OH
Ia1.108OCH 3HCH(CH 3 )SO 2 CH 3OH
Ia1.109OCH 3HCH(CH 3 )SO 2 CH 2 CH 3OH
Ia1.110OCH 2HCH(CH 3 )SO 2 CH(CH 3 ) 2OH
Ia1.111OCH 3HCH(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ia1.112OCH 3HCH(CH 3 )ClOH
Ia1.113OCH 3HCH(CH 3 )BrOH
Ia1.114OCH 3HCH(CH 3 )NO 2OH
Ia1.115OCH 3HCH(CH 3 )CHF 2OH
Ia1.116OCH 3HCH(CH 3 )CF 3OH
Ia1.117OCH 3HCH(CH 3 )OCH 3OH
Ia1.118OCH 3HCH(CH 3 )OCH 2 CH 3OH
Ia1.119OCH 3HCH(CH 3 )OCHF 2OH
Ia1.120OCH 3HCH(CH 3 )OCF 3OH
Ia1.121OCH 3CH 3CH(CH 3 )SCH 3OH
Ia1.122OCH 3CH 3CH(CH 3 )SCH 2 CH 3OH
Ia1.123OCH 3CH 3CH(CH 3 )SO 2 CH 3OH
Ia1.124OCH 3CH 3CH(CH 3 )SO 2 CH 2 CH 3OH
Ia1.125OCH 3CH 3CH(CH 3 )SO 2 CH(CH 3 ) 2OH
Ia1.126OCH 3CH 3CH(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ia1.127OCH 3CH 3CH(CH 3 )ClOH
Ia1.128OCH 3CH 3CH(CH 3 )BrOH
Ia1.129OCH 3CH 3CH(CH 3 )NO 2OH
Ia1.130OCH 3CH 3CH(CH 3 )CHF 2OH
Ia1.131OCH 3CH 3CH(CH 3 )CF 3OH
Ia1.132OCH 3CH 3CH(CH 3 )OCH 3OH
Ia1.133OCH 3CH 3CH(CH 3 )OCH 2 CH 3OH
Ia1.134OCH 3CH 3CH(CH 3 )OCHF 2OH
Ia1.135OCH 3CH 3CH(CH 3 )OCF 3OH
Ia1.136OHHC(CH 3 ) 2SCH 3OH
Ia1.137OHHC(CH 3 ) 2SCH 2 CH 3OH
Ia1.138OHHC(CH 3 ) 2SO 2 CH 3OH
Ia1.139OHHC(CH 3 ) 2SO 2 CH 2 CH 3OH
Ia1.140OHHC(CH 3 ) 2SO 2 CH(CH 3 ) 2OH
Ia1.141OHHC(CH 3 ) 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.142OHHC(CH 3 ) 2ClOH
Ia1.143OHHC(CH 3 ) 2BrOH
Ia1.144OHHC(CH 3 ) 2NO 2OH
Ia1.145OHHC(CH 3 ) 2CHF 2OH
Ia1.146OHHC(CH 3 ) 2CF 3OH
Ia1.147OHHC(CH 3 ) 2OCH 3OH
Ia1.148OHHC(CH 3 ) 2OCH 2 CH 3OH
Ia1.149OHHC(CH 3 ) 2OCHF 2OH
Ia1.150OHHC(CH 3 ) 2OCF 3OH
Ia1.151OCH 3HC(CH 3 ) 2SCH 3OH
Ia1.152OCH 3HC(CH 3 ) 2SCH 2 CH 3OH
Ia1.153OCH 3HC(CH 3 ) 2SO 2 CH 3OH
Ia1.154OCH 3HC(CH 3 ) 2SO 2 CH 2 CH 3OH
Ia1.155OCH 3HC(CH 3 ) 2SO 2 CH(CH 3 ) 2OH
Ia1.156OCH 3HC(CH 3 ) 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.157OCH 3HC(CH 3 ) 2ClOH
Ia1.158OCH 3HC(CH 3 ) 2BrOH
Ia1.159OCH 3HC(CH 3 ) 2NO 2OH
Ia1.160OCH 3HC(CH 3 ) 2CHF 2OH
Ia1.161OCH 3HC(CH 3 ) 2CF 3OH
Ia1.162OCH 3HC(CH 3 ) 2OCH 3OH
Ia1.163OCH 3HC(CH 3 ) 2OCH 2 CH 3OH
Ia1.164OCH 3HC(CH 3 ) 2OCHF 2OH
Ia1.165OCH 3HC(CH 3 ) 2OCF 3OH
Ia1.166OCH 3CH 3C(CH 3 ) 2SCH 3OH
Ia1.167OCH 3CH 3C(CH 3 ) 2SCH 2 CH 3OH
Ia1.168OCH 3CH 3C(CH 3 ) 2SO 2 CH 3OH
Ia1.169OCH 3CH 3C(CH 3 ) 2SO 2 CH 2 CH 3OH
Ia1.170OCH 3CH 3C(CH 3 ) 2SO 2 CH(CH 3 ) 2OH
Ia1.171OCH 3CH 3C(CH 3 ) 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.172OCH 3CH 3C(CH 3 ) 2ClOH
Ia1.173OCH 3CH 3C(CH 3 ) 2BrOH
Ia1.174OCH 3CH 3C(CH 3 ) 2NO 2OH
Ia1.175OCH 3CH 3C(CH 3 ) 2CHF 2OH
Ia1.176OCH 3CH 3C(CH 3 ) 2CF 3OH
Ia1.177OCH 3CH 3C(CH 3 ) 2OCH 3OH
Ia1.178OCH 3CH 3C(CH 3 ) 2OCH 2 CH 3OH
Ia1.179OCH 3CH 3C(CH 3 ) 2OCHF 2OH
Ia1.180OCH 3CH 3C(CH 3 ) 2OCF 3OH
Ia1.181NCH 3HHCH 2SCH 3OH
Ia1.182NCH 3HHCH 2SCH 2 CH 3OH
Ia1.183NCH 3HHCH 2SO 2 CH 3OH
Ia1.184NCH 3HHCH 2SO 2 CH 2 CH 3OH
Ia1.185NCH 3HHCH 2SO 2 CH(CH 3 ) 2OH
Ia1.186NCH 3HHCH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.187NCH 3HHCH 2ClOH
Ia1.188NCH 3HHCH 2BrOH
Ia1.189NCH 3HHCH 2NO 2OH
Ia1.190NCH 3HHCH 2CHF 2OH
Ia1.191NCH 3HHCH 2CF 3OH
Ia1.192NCH 3HHCH 2OCH 3OH
Ia1.193NCH 3HHCH 2OCH 2 CH 3OH
Ia1.194NCH 3HHCH 2OCHF 2OH
Ia1.195NCH 3HHCH 2OCF 3OH
Ia1.196NCH 3CH 3HCH 2SCH 3OH
Ia1.197NCH 3CH 3HCH 2SCH 2 CH 3OH
Ia1.198NCH 3CH 3HCH 2SO 2 CH 3OH
Ia1.199NCH 3CH 3HCH 2SO 2 CH 2 CH 3OH
Ia1.200NCH 3CH 3HCH 2SO 2 CH(CH 3 ) 2OH
Ia1.201NCH 3CH 3HCH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.202NCH 3CH 3HCH 2ClOH
Ia1.203NCH 3CH 3HCH 2BrOH
Ia1.204NCH 3CH 3HCH 2NO 2OH
Ia1.205NCH 3CH 3HCH 2CHF 2OH
Ia1.206NCH 3CH 3HCH 2CF 3OH
Ia1.207NCH 3CH 3HCH 2OCH 3OH
Ia1.208NCH 3CH 3HCH 2OCH 2 CH 3OH
Ia1.209NCH 3CH 3HCH 2OCHF 2OH
Ia1.210NCH 3CH 3HCH 2OCF 3OH
Ia1.211NCH 3CH 3CH 3CH 2SCH 3OH
Ia1.212NCH 3CH 3CH 3CH 2SCH 2 CH 3OH
Ia1.213NCH 3CH 3CH 3CH 2SO 2 CH 3OH
Ia1.214NCH 3CH 3CH 3CH 2SO 2 CH 2 CH 3OH
Ia1.215NCH 3CH 3CH 3CH 2SO 2 CH(CH 3 ) 2OH
Ia1.216NCH 3CH 3CH 3CH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.217NCH 3CH 3CH 3CH 2ClOH
Ia1.218NCH 3CH 3CH 3CH 2BrOH
Ia1.219NCH 3CH 3CH 3CH 2NO 2OH
Ia1.220NCH 3CH 3CH 3CH 2CHF 2OH
Ia1.221NCH 3CH 3CH 3CH 2CF 3OH
Ia1.222NCH 3CH 3CH 3CH 2OCH 3OH
Ia1.223NCH 3CH 3CH 3CH 2OCH 2 CH 3OH
Ia1.224NCH 3CH 3CH 3CH 2OCHF 2OH
Ia1.225NCH 3CH 3CH 3CH 2OCF 3OH
Ia1.226NCH 3CH 2 ClHCH 2SCH 3OH
Ia1.227NCH 3CH 2 ClHCH 2SCH 2 CH 3OH
Ia1.228NCH 3CH 2 ClHCH 2SO 2 CH 3OH
Ia1.229NCH 3CH 2 ClHCH 2SO 2 CH 2 CH 3OH
Ia1.230NCH 3CH 2 ClHCH 2SO 2 CH(CH 3 ) 2OH
Ia1.231NCH 3CH 2 ClHCH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.232NCH 3CH 2 ClHCH 2ClOH
Ia1.233NCH 3CH 2 ClHCH 2BrOH
Ia1.234NCH 3CH 2 ClHCH 2NO 2OH
Ia1.235NCH 3CH 2 ClHCH 2CHF 2OH
Ia1.236NCH 3CH 2 ClHCH 2CF 3OH
Ia1.237NCH 3CH 2 ClHCH 2OCH 3OH
Ia1.238NCH 3CH 2 ClHCH 2OCH 2 CH 3OH
Ia1.239NCH 3CH 2 ClHCH 2OCHF 2OH
Ia1.240NCH 3CH 2 ClHCH 2OCF 3OH
Ia1.241NCH 3CH 2 CH 3HCH 2SCH 3OH
Ia1.242NCH 3CH 2 CH 3HCH 2SCH 2 CH 3OH
Ia1.243NCH 3CH 2 CH 3HCH 2SO 2 CH 3OH
Ia1.244NCH 3CH 2 CH 3HCH 2SO 2 CH 2 CH 3OH
Ia1.245NCH 3CH 2 CH 3HCH 2SO 2 CH(CH 3 ) 2OH
Ia1.246NCH 3CH 2 CH 3HCH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.247NCH 3CH 2 CH 3HCH 2ClOH
Ia1.248NCH 3CH 2 CH 3HCH 2BrOH
Ia1.249NCH 3CH 2 CH 3HCH 2NO 2OH
Ia1.250NCH 3CH 2 CH 3HCH 2CHF 2OH
Ia1.251NCH 3CH 2 CH 3HCH 2CF 3OH
Ia1.252NCH 3CH 2 CH 3HCH 2OCH 3OH
Ia1.253NCH 3CH 2 CH 3HCH 2OCH 2 CH 3OH
Ia1.254NCH 3CH 2 CH 3HCH 2OCHF 2OH
Ia1.255NCH 3CH 2 CH 3HCH 2OCF 3OH
Ia1.256NCH 3CH 2 CH 3CH 2 CH 3CH 2SCH 3OH
Ia1.257NCH 3CH 2 CH 3CH 2 CH 3CH 2SCH 2 CH 3OH
Ia1.258NCH 3CH 2 CH 3CH 2 CH 3CH 2SO 2 CH 3OH
Ia1.259NCH 3CH 2 CH 3CH 2 CH 3CH 2SO 2 CH 2 CH 3OH
Ia1.260NCH 3CH 2 CH 3CH 2 CH 3CH 2SO 2 CH(CH 3 ) 2OH
Ia1.261NCH 3CH 2 CH 3CH 2 CH 3CH 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.262NCH 3CH 2 CH 3CH 2 CH 3CH 2ClOH
Ia1.263NCH 3CH 2 CH 3CH 2 CH 3CH 2BrOH
Ia1.264NCH 3CH 2 CH 3CH 2 CH 3CH 2NO 2OH
Ia1.265NCH 3CH 2 CH 3CH 2 CH 3CH 2CHF 2OH
Ia1.266NCH 3CH 2 CH 3CH 2 CH 3CH 2CF 3OH
Ia1.267NCH 3CH 2 CH 3CH 2 CH 3CH 2OCH 3OH
Ia1.268NCH 3CH 2 CH 3CH 2 CH 3CH 2OCH 2 CH 3OH
Ia1.269NCH 3CH 2 CH 3CH 2 CH 3CH 2OCHF 2OH
Ia1.270NCH 3CH 2 CH 3CH 2 CH 3CH 2OCF 3OH
Ia1.271NCH 3HHCH(CH 3 )SCH 3OH
Ia1.272NCH 3HHCH(CH 3 )SCH 2 CH 3OH
Ia1.273NCH 3HHCH(CH 3 )SO 2 CH 3OH
Ia1.274NCH 3HHCH(CH 3 )SO 2 CH 2 CH 3OH
Ia1.275NCH 3HHCH(CH 3 )SO 2 CH(CH 3 ) 2OH
Ia1.276NCH 3HHCH(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ia1.277NCH 3HHCH(CH 3 )ClOH
Ia1.278NCH 3HHCH(CH 3 )BrOH
Ia1.279NCH 3HHCH(CH 3 )NO 2OH
Ia1.280NCH 3HHCH(CH 3 )CHF 2OH
Ia1.281NCH 3HHCH(CH 3 )CF 3OH
Ia1.282NCH 3HHCH(CH 3 )OCH 3OH
Ia1.283NCH 3HHCH(CH 3 )OCH 2 CH 3OH
Ia1.284NCH 3HHCH(CH 3 )OCHF 2OH
Ia1.285NCH 3HHCH(CH 3 )OCF 3OH
Ia1.286NCH 3CH 3HCH(CH 3 )SCH 3OH
Ia1.287NCH 3CH 3HCH(CH 3 )SCH 2 CH 3OH
Ia1.288NCH 3CH 3HCH(CH 3 )SO 2 CH 3OH
Ia1.289NCH 3CH 3HCH(CH 3 )SO 2 CH 2 CH 3OH
Ia1.290NCH 3CH 3HCH(CH 3 )SO 2 CH(CH 3 ) 2OH
Ia1.291NCH 3CH 3HCH(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ia1.292NCH 3CH 3HCH(CH 3 )ClOH
Ia1.293NCH 3CH 3HCH(CH 3 )BrOH
Ia1.294NCH 3CH 3HCH(CH 3 )NO 2OH
Ia1.295NCH 3CH 3HCH(CH 3 )CHF 2OH
Ia1.296NCH 3CH 3HCH(CH 3 )CF 3OH
Ia1.297NCH 3CH 3HCH(CH 3 )OCH 3OH
Ia1.298NCH 3CH 3HCH(CH 3 )OCH 2 CH 3OH
Ia1.299NCH 3CH 3HCH(CH 3 )OCHF 2OH
Ia1.300NCH 3CH 3HCH(CH 3 )OCF 3OH
Ia1.301NCH 3CH 3CH 3CH(CH 3 )SCH 3OH
Ia1.302NCH 3CH 3CH 3CH(CH 3 )SCH 2 CH 3OH
Ia1.303NCH 3CH 3CH 3CH(CH 3 )SO 2 CH 3OH
Ia1.304NCH 3CH 3CH 3CH(CH 3 )SO 2 CH 2 CH 3OH
Ia1.305NCH 3CH 3CH 3CH(CH 3 )SO 2 CH(CH 3 ) 2OH
Ia1.306NCH 3CH 3CH 3CH(CH 3 )SO 2 (CH 2 ) 2 H 3OH
Ia1.307NCH 3CH 3CH 3CH(CH 3 )ClOH
Ia1.308NCH 3CH 3CH 3CH(CH 3 )BrOH
Ia1.309NCH 3CH 3CH 3CH(CH 3 )NO 2OH
Ia1.310NCH 3CH 3CH 3CH(CH 3 )CHF 2OH
Ia1.311NCH 3CH 3CH 3CH(CH 3 )CF 3OH
Ia1.312NCH 3CH 3CH 3CH(CH 3 )OCH 3OH
Ia1.313NCH 3CH 3CH 3CH(CH 3 )OCH 2 CH 3OH
Ia1.314NCH 3CH 3CH 3CH(CH 3 )OCHF 2OH
Ia1.315NCH 3CH 3CH 3CH(CH 3 )OCF 3OH
Ia1.316NCH 3HHC(CH 3 ) 2SCH 3OH
Ia1.317NCH 3HHC(CH 3 ) 2SCH 2 CH 3OH
Ia1.318NCH 3HHC(CH 3 ) 2SO 2 CH 3OH
Ia1.319NCH 3HHC(CH 3 ) 2SO 2 CH 2 CH 3OH
Ia1.320NCH 3HHC(CH 3 ) 2SO 2 CH(CH 3 ) 2OH
Ia1.321NCH 3HHC(CH 3 ) 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.322NCH 3HHC(CH 3 ) 2ClOH
Ia1.323NCH 3HHC(CH 3 ) 2BrOH
Ia1.324NCH 3HHC(CH 3 ) 2NO 2OH
Ia1.325NCH 3HHC(CH 3 ) 2CHF 2OH
Ia1.326NCH 3HHC(CH 3 ) 2CF 3OH
Ia1.327NCH 3HHC(CH 3 ) 2OCH 3OH
Ia1.328NCH 3HHC(CH 3 ) 2OCH 2 CH 3OH
Ia1.329NCH 3HHC(CH 3 ) 2OCHF 2OH
Ia1.330NCH 3HHC(CH 3 ) 2OCF 3OH
Ia1.331NCH 3CH 3HC(CH 3 ) 2SCH 3OH
Ia1.332NCH 3CH 3HC(CH 3 ) 2SCH 2 CH 3OH
Ia1.333NCH 3CH 3HC(CH 3 ) 2SO 2 CH 3OH
Ia1.334NCH 3CH 3HC(CH 3 ) 2SO 2 CH 2 CH 3OH
Ia1.335NCH 3CH 3HC(CH 3 ) 2SO 2 CH(CH 3 ) 2OH
Ia1.336NCH 3CH 3HC(CH 3 ) 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.337NCH 3CH 3HC(CH 3 ) 2ClOH
Ia1.338NCH 3CH 3HC(CH 3 ) 2BrOH
Ia1.339NCH 3CH 3HC(CH 3 ) 2NO 2OH
Ia1.340NCH 3CH 3HC(CH 3 ) 2CHF 2OH
Ia1.341NCH 3CH 3HC(CH 3 ) 2CF 3OH
Ia1.342NCH 3CH 3HC(CH 3 ) 2OCH 3OH
Ia1.343NCH 3CH 3HC(CH 3 ) 2OCH 2 CH 3OH
Ia1.344NCH 3CH 3HC(CH 3 ) 2OCHF 2OH
Ia1.345NCH 3CH 3HC(CH 3 ) 2OCF 3OH
Ia1.346NCH 3CH 3CH 3C(CH 3 ) 2SCH 3OH
Ia1.347NCH 3CH 3CH 3C(CH 3 ) 2SCH 2 CH 3OH
Ia1.348NCH 3CH 3CH 3C(CH 3 ) 2SO 2 CH 3OH
Ia1.349NCH 3CH 3CH 3C(CH 3 ) 2SO 2 CH 2 CH 3OH
Ia1.350NCH 3CH 3CH 3C(CH 3 ) 2SO 2 CH(CH 3 ) 2OH
Ia1.351NCH 3CH 3CH 3C(CH 3 ) 2SO 2 (CH 2 ) 2 CH 3OH
Ia1.352NCH 3CH 3CH 3C(CH 3 ) 2ClOH
Ia1.353NCH 3CH 3CH 3C(CH 3 ) 2BrOH
Ia1.354NCH 3CH 3CH 3C(CH 3 ) 2NO 2OH
Ia1.355NCH 3CH 3CH 3C(CH 3 ) 2CHF 2OH
Ia1.356NCH 3CH 3CH 3C(CH 3 ) 2CF 3OH
Ia1.357NCH 3CH 3CH 3C(CH 3 ) 2OCH 3OH
Ia1.358NCH 3CH 3CH 3C(CH 3 ) 2OCH 2 CH 3OH
Ia1.359NCH 3CH 3CH 3C(CH 3 ) 2OCHF 2OH
Ia1.360NCH 3CH 3CH 3C(CH 3 ) 2OCF 3OH
Ia1.361CH 2HHOSCH 3OH
Ia1.362CH 2HHOSCH 2 CH 3OH
Ia1.363CH 2HHOSO 2 CH 3OH
Ia1.364CH 2HHOSO 2 CH 2 CH 3OH
Ia1.365CH 2HHOSO 2 CH(CH 3 ) 2OH
Ia1.366CH 2HHOSO 2 (CH 2 ) 2 CH 3OH
Ia1.367CH 2HHOClOH
Ia1.368CH 2HHOBrOH
Ia1.369CH 2HHONO 2OH
Ia1.370CH 2HHOCHF 2OH
Ia1.371CH 2HHOCF 3OH
Ia1.372CH 2HHOOCH 3OH
Ia1.373CH 2HHOOCH 2 CH 3OH
Ia1.374CH 2HHOOCHF 2OH
Ia1.375CH 2HHOOCF 3OH
Ia1.376CH 2CH 3HOSCH 3OH
Ia1.377CH 2CH 3HOSCH 2 CH 3OH
Ia1.378CH 2CH 3HOSO 2 CH 3OH
Ia1.379CH 2CH 3HOSO 2 CH 2 CH 3OH
Ia1.380CH 2CH 3HOSO 2 CH(CH 3 ) 2OH
Ia1.381CH 2CH 3HOSO 2 (CH 2 ) 2 CH 3OH
Ia1.382CH 2CH 3HOClOH
Ia1.383CH 2CH 3HOBrOH
Ia1.384CH 2CH 3HONO 2OH
Ia1.385CH 2CH 3HOCHF 2OH
Ia1.386CH 2CH 3HOCF 3OH
Ia1.387CH 2CH 3HOOCH 3OH
Ia1.388CH 2CH 3HOOCH 2 CH 3OH
Ia1.389CH 2CH 3HOOCHF 2OH
Ia1.390CH 2CH 3HOOCF 3OH
Ia1.391CH 2CH 3CH 3OSCH 3OH
Ia1.392CH 2CH 3CH 3OSCH 2 CH 3OH
Ia1.393CH 2CH 3CH 3OSO 2 CH 3OH
Ia1.394CH 2CH 3CH 3OSO 2 CH 2 CH 3OH
Ia1.395CH 2CH 3CH 3OSO 2 CH(CH 3 ) 2OH
Ia1.396CH 2CH 3CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ia1.397CH 2CH 3CH 3OClOH
Ia1.398CH 2CH 3CH 3OBrOH
Ia1.399CH 2CH 3CH 3ONO 2OH
Ia1.400CH 2CH 3CH 3OCHF 2OH
Ia1.401CH 2CH 3CH 3OCF 3OH
Ia1.402CH 2CH 3CH 3OOCH 3OH
Ia1.403CH 2CH 3CH 3OOCH 2 CH 3OH
Ia1.404CH 2CH 3CH 3OOCHF 2OH
Ia1.405CH 2CH 3CH 3OOCF 3OH
Ia1.406CH 2HHSSCH 3OH
Ia1.407CH 2HHSSCH 2 CH 3OH
Ia1.408CH 2HHSSO 2 CH 3OH
Ia1.409CH 2HHSSO 2 CH 2 CH 3OH
Ia1.410CH 2HHSSO 2 CH(CH 3 ) 2OH
Ia1.411CH 2HHSSO 2 (CH 2 ) 2 CH 3OH
Ia1.412CH 2HHSClOH
Ia1.413CH 2HHSBrOH
Ia1.414CH 2HHSNO 3OH
Ia1.415CH 2HHSCHF 2OH
Ia1.416CH 2HHSCF 3OH
Ia1.417CH 2HHSOCH 3OH
Ia1.418CH 2HHSOCH 2 CH 3OH
Ia1.419CH 2HHSOCHF 2OH
Ia1.420CH 2HHSOCF 3OH
Ia1.421CH 2CH 3HSSCH 3OH
Ia1.422CH 2CH 3HSSCH 2 CH 3OH
Ia1.423CH 2CH 3HSSO 2 CH 3OH
Ia1.424CH 2CH 3HSSO 2 CH 2 CH 3OH
Ia1.425CH 2CH 3HSSO 2 CH(CH 3 ) 2OH
Ia1.426CH 2CH 3HSSO 2 (CH 2 ) 2 CH 3OH
Ia1.427CH 2CH 3HSClOH
Ia1.428CH 2CH 3HSBrOH
Ia1.429CH 2CH 3HSNO 2OH
Ia1.430CH 2CH 3HSCHF 2OH
Ia1.431CH 2CH 3HSCF 3OH
Ia1.432CH 2CH 3HSOCH 3OH
Ia1.433CH 2CH 3HSOCH 2 CH 3OH
Ia1.434CH 2CH 3HSOCHF 2OH
Ia1.435CH 2CH 3HSOCF 3OH
Ia1.436CH 2CH 3CH 3SSCH 3OH
Ia1.437CH 2CH 3CH 3SSCH 2 CH 3OH
Ia1.438CH 2CH 3CH 3SSO 2 CH 3OH
Ia1.439CH 2CH 3CH 3SSO 2 CH 2 CH 3OH
Ia1.440CH 2CH 3CH 3SSO 2 CH(CH 3 ) 2OH
Ia1.441CH 2CH 3CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ia1.442CH 2CH 3CH 3SClOH
Ia1.443CH 2CH 3CH 3SBrOH
Ia1.444CH 2CH 3CH 3SNO 2OH
Ia1.445CH 2CH 3CH 3SCHF 2OH
Ia1.446CH 2CH 3CH 3SCF 3OH
Ia1.447CH 2CH 3CH 3SOCH 3OH
Ia1.448CH 2CH 3CH 3SOCH 2 CH 3OH
Ia1.449CH 2CH 3CH 3SOCHF 2OH
Ia1.450CH 2CH 3CH 3SOCF 3OH
Ia1.451CH 2HHNCH 3SCH 3OH
Ia1.452CH 2HHNCH 3SCH 2 CH 3OH
Ia1.453CH 2HHNCH 3SO 2 CH 3OH
Ia1.454CH 2HHNCH 3SO 2 CH 2 CH 3OH
Ia1.455CH 2HHNCH 3SO 2 CH(CH 3 ) 2OH
Ia1.456CH 2HHNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.457CH 2HHNCH 3ClOH
Ia1.458CH 2HHNCH 3BrOH
Ia1.459CH 2HHNCH 3NO 2OH
Ia1.460CH 2HHNCH 3CHF 2OH
Ia1.461CH 2HHNCH 3CF 3OH
Ia1.462CH 2HHNCH 3OCH 3OH
Ia1.463CH 2HHNCH 3OCH 2 CH 3OH
Ia1.464CH 2HHNCH 3OCHF 2OH
Ia1.465CH 2HHNCH 3OCF 3OH
Ia1.466CH 2CH 3HNCH 3SCH 3OH
Ia1.467CH 2CH 3HNCH 3SCH 2 CH 3OH
Ia1.468CH 2CH 3HNCH 3SO 2 CH 3OH
Ia1.469CH 2CH 3HNCH 3SO 2 CH 2 CH 3OH
Ia1.470CH 2CH 3HNCH 3SO 2 CH(CH 3 ) 2OH
Ia1.471CH 2CH 3HNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.472CH 2CH 3HNCH 3ClOH
Ia1.473CH 2CH 3HNCH 3BrOH
Ia1.474CH 2CH 3HNCH 3NO 2OH
Ia1.475CH 2CH 3HNCH 3CHF 2OH
Ia1.476CH 2CH 3HNCH 3CF 3OH
Ia1.477CH 2CH 3HNCH 3OCH 3OH
Ia1.478CH 2CH 3HNCH 3OCH 2 CH 3OH
Ia1.479CH 2CH 3HNCH 3OCHF 2OH
Ia1.480CH 2CH 3HNCH 3OCF 3OH
Ia1.481CH 2CH 3CH 3NCH 3SCH 3OH
Ia1.482CH 2CH 3CH 3NCH 3SCH 2 CH 3OH
Ia1.483CH 2CH 3CH 3NCH 3SO 2 CH 3OH
Ia1.484CH 2CH 3CH 3NCH 3SO 2 CH 2 CH 3OH
Ia1.485CH 2CH 3CH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ia1.486CH 2CH 3CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.487CH 2CH 3CH 3NCH 3ClOH
Ia1.488CH 2CH 3CH 3NCH 3BrOH
Ia1.489CH 2CH 3CH 3NCH 3NO 2OH
Ia1.490CH 2CH 3CH 3NCH 3CHF 2OH
Ia1.491CH 2CH 3CH 3NCH 3CF 3OH
Ia1.492CH 2CH 3CH 3NCH 3OCH 3OH
Ia1.493CH 2CH 3CH 3NCH 3OCH 2 CH 3OH
Ia1.494CH 2CH 3CH 3NCH 3OCHF 2OH
Ia1.495CH 2CH 3CH 3NCH 3OCF 3OH
Ia1.496CHCH 3HHOSCH 3OH
Ia1.497CHCH 3HHOSCH 2 CH 3OH
Ia1.498CHCH 3HHOSO 2 CH 3OH
Ia1.499CHCH 3HHOSO 2 CH 2 CH 3OH
Ia1.500CHCH 3HHOSO 2 CH(CH 3 ) 2OH
Ia1.501CHCH 3HHOSO 2 (CH 2 ) 2 CH 3OH
Ia1.502CHCH 3HHOClOH
Ia1.503CHCH 3HHOBrOH
Ia1.504CHCH 3HHONO 2OH
Ia1.505CHCH 3HHOCHF 2OH
Ia1.506CHCH 3HHOCF 3OH
Ia1.507CHCH 3HHOOCH 3OH
Ia1.508CHCH 3HHOOCH 2 CH 3OH
Ia1.509CHCH 3HHOOCHF 2OH
Ia1.510CHCH 3HHOOCF 3OH
Ia1.511CHCH 3CH 3HOSCH 3OH
Ia1.512CHCH 3CH 3HOSCH 2 CH 3OH
Ia1.513CHCH 3CH 3HOSO 2 CH 3OH
Ia1.514CHCH 3CH 3HOSO 2 CH 2 CH 3OH
Ia1.515CHCH 3CH 3HOSO 2 CH(CH 3 ) 2OH
Ia1.516CHCH 3CH 3HOSO 2 (CH 2 ) 2 CH 3OH
Ia1.517CHCH 3CH 3HOClOH
Ia1.518CHCH 3CH 3HOBrOH
Ia1.519CHCH 3CH 3HONO 2OH
Ia1.520CHCH 3CH 3HOCHF 2OH
Ia1.521CHCH 3CH 3HOCF 3OH
Ia1.522CHCH 3CH 3HOOCH 3OH
Ia1.523CHCH 3CH 3HOOCH 2 CH 3OH
Ia1.524CHCH 3CH 3HOOCHF 2OH
Ia1.525CHCH 3CH 3HOOCF 3OH
Ia1.526CHCH 3CH 3CH 3OSCH 3OH
Ia1.527CHCH 3CH 3CH 3OSCH 2 CH 3OH
Ia1.528CHCH 3CH 3CH 3OSO 2 CH 3OH
Ia1.529CHCH 3CH 3CH 3OSO 2 CH 2 CH 3OH
Ia1.530CHCH 3CH 3CH 3OSO 2 CH(CH 3 ) 2OH
Ia1.531CHCH 3CH 3CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ia1.532CHCH 3CH 3CH 3OClOH
Ia1.533CHCH 3CH 3CH 3OBrOH
Ia1.534CHCH 3CH 3CH 3ONO 2OH
Ia1.535CHCH 3CH 3CH 3OCHF 2OH
Ia1.536CHCH 3CH 3CH 3OCF 3OH
Ia1.537CHCH 3CH 3CH 3OOCH 3OH
Ia1.538CHCH 3CH 3CH 3OOCH 2 CH 3OH
Ia1.539CHCH 3CH 3CH 3OOCHF 2OH
Ia1.540CHCH 3CH 3CH 3OOCF 3OH
Ia1.541CHCH 3HHSSCH 3OH
Ia1.542CHCH 3HHSSCH 2 CH 3OH
Ia1.543CHCH 3HHSSO 2 CH 3OH
Ia1.544CHCH 3HHSSO 2 CH 2 CH 3OH
Ia1.545CHCH 3HHSSO 2 CH(CH 3 ) 2OH
Ia1.546CHCH 3HHSSO 2 (CH 2 ) 2 CH 3OH
Ia1.547CHCH 3HHSClOH
Ia1.548CHCH 3HHSBrOH
Ia1.549CHCH 3HHSNO 2OH
Ia1.550CHCH 3HHSCHF 2OH
Ia1.551CHCH 3HHSCF 3OH
Ia1.552CHCH 3HHSOCH 3OH
Ia1.553CHCH 3HHSOCH 2 CH 3OH
Ia1.554CHCH 3HHSOCHF 2OH
Ia1.555CHCH 3HHSOCF 3OH
Ia1.556CHCH 3CH 3HSSCH 3OH
Ia1.557CHCH 3CH 3HSSCH 2 CH 3OH
Ia1.558CHCH 3CH 3HSSO 2 CH 3OH
Ia1.559CHCH 3CH 3HSSO 2 CH 2 CH 3OH
Ia1.560CHCH 3CH 3HSSO 2 CH(CH 3 ) 2OH
Ia1.561CHCH 3CH 3HSSO 2 (CH 2 ) 2 CH 3OH
Ia1.562CHCH 3CH 3HSClOH
Ia1.563CHCH 3CH 3HSBrOH
Ia1.564CHCH 3CH 3HSNO 2OH
Ia1.565CHCH 3CH 3HSCHF 2OH
Ia1.566CHCH 3CH 3HSCF 3OH
Ia1.567CHCH 3CH 3HSOCH 3OH
Ia1.568CHCH 3CH 3HSOCH 2 CH 3OH
Ia1.569CHCH 3CH 3HSOCHF 2OH
Ia1.570CHCH 3CH 3HSOCF 3OH
Ia1.571CHCH 3CH 3CH 3SSCH 3OH
Ia1.572CHCH 3CH 3CH 3SSCH 2 CH 3OH
Ia1.573CHCH 3CH 3CH 3SSO 2 CH 3OH
Ia1.574CHCH 3CH 3CH 3SSO 2 CH 2 CH 3OH
Ia1.575CHCH 3CH 3CH 3SSO 2 CH(CH 3 ) 2OH
Ia1.576CHCH 3CH 3CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ia1.577CHCH 3CH 3CH 3SClOH
Ia1.578CHCH 3CH 3CH 3SBrOH
Ia1.579CHCH 3CH 3CH 3SNO 2OH
Ia1.580CHCH 3CH 3CH 3SCHF 2OH
Ia1.581CHCH 3CH 3CH 3SCF 3OH
Ia1.582CHCH 3CH 3CH 3SOCH 3OH
Ia1.583CHCH 3CH 3CH 3SOCH 2 CH 3OH
Ia1.584CHCH 3CH 3CH 3SOCHF 2OH
Ia1.585CHCH 3CH 3CH 3SOCF 3OH
Ia1.586CHCH 3HHNCH 3SCH 3OH
Ia1.587CHCH 3HHNCH 3SCH 2 CH 3OH
Ia1.588CHCH 3HHNCH 3SO 2 CH 3OH
Ia1.589CHCH 3HHNCH 3SO 2 CH 2 CH 3OH
Ia1.590CHCH 3HHNCH 3SO 2 CH(CH 3 ) 2OH
Ia1.591CHCH 3HHNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.592CHCH 3HHNCH 3ClOH
Ia1.593CHCH 3HHNCH 3BrOH
Ia1.594CHCH 3HHNCH 3NO 2OH
Ia1.595CHCH 3HHNCH 3CHF 2OH
Ia1.596CHCH 3HHNCH 3CF 3OH
Ia1.597CHCH 3HHNCH 3OCH 3OH
Ia1.598CHCH 3HHNCH 3OCH 2 CH 3OH
Ia1.599CHCH 3HHNCH 3OCHF 2OH
Ia1.600CHCH 3HHNCH 3OCF 3OH
Ia1.601CHCH 3CH 3HNCH 3SCH 3OH
Ia1.602CHCH 3CH 3HNCH 3SCH 2 CH 3OH
Ia1.603CHCH 3CH 3HNCH 3SO 2 CH 3OH
Ia1.604CHCH 3CH 3HNCH 3SO 2 CH 2 CH 3OH
Ia1.605CHCH 3CH 3HNCH 3SO 2 CH(CH 3 ) 2OH
Ia1.606CHCH 3CH 3HNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.607CHCH 3CH 3HNCH 3ClOH
Ia1.608CHCH 3CH 3HNCH 3BrOH
Ia1.609CHCH 3CH 3HNCH 3NO 2OH
Ia1.610CHCH 3CH 3HNCH 3CHF 2OH
Ia1.611CHCH 3CH 3HNCH 3CF 3OH
Ia1.612CHCH 3CH 3HNCH 3OCH 3OH
Ia1.613CHCH 3CH 3HNCH 3OCH 2 CH 3OH
Ia1.614CHCH 3CH 3HNCH 3OCHF 2OH
Ia1.615CHCH 3CH 3HNCH 3OCF 3OH
Ia1.616CHCH 3CH 3CH 3NCH 3SCH 3OH
Ia1.617CHCH 3CH 3CH 3NCH 3SCH 2 CH 3OH
Ia1.618CHCH 3CH 3CH 3NCH 3SO 2 CH 3OH
Ia1.619CHCH 3CH 3CH 3NCH 3SO 2 CH 2 CH 3OH
Ia1.620CHCH 3CH 3CH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ia1.621CHCH 3CH 3CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.622CHCH 3CH 3CH 3NCH 3ClOH
Ia1.623CHCH 3CH 3CH 3NCH 3BrOH
Ia1.624CHCH 3CH 3CH 3NCH 3NO 2OH
Ia1.625CHCH 3CH 3CH 3NCH 3CHF 2OH
Ia1.626CHCH 3CH 3CH 3NCH 3CF 3OH
Ia1.627CHCH 3CH 3CH 3NCH 3OCH 3OH
Ia1.628CHCH 3CH 3CH 3NCH 3OCH 2 CH 3OH
Ia1.629CHCH 3CH 3CH 3NCH 3OCHF 2OH
Ia1.630CHCH 3CH 3CH 3NCH 3OCF 3OH
Ia1.631C(CH 3 ) 2HHOSCH 3OH
Ia1.632C(CH 3 ) 2HHOSCH 2 CH 3OH
Ia1.633C(CH 3 ) 2HHOSO 2 CH 3OH
Ia1.634C(CH 3 ) 2HHOSO 2 CH 2 CH 3OH
Ia1.635C(CH 3 ) 2HHOSO 2 CH(CH 3 ) 2OH
Ia1.636C(CH 3 ) 2HHOSO 2 (CH 2 ) 2 CH 3OH
Ia1.637C(CH 3 ) 2HHOClOH
Ia1.638C(CH 3 ) 2HHOBrOH
Ia1.639C(CH 3 ) 2HHONO 2OH
Ia1.640C(CH 3 ) 2HHOCHF 2OH
Ia1.641C(CH 3 ) 2HHOCF 3OH
Ia1.642C(CH 3 ) 2HHOOCH 3OH
Ia1.643C(CH 3 ) 2HHOOCH 2 CH 3OH
Ia1.644C(CH 3 ) 2HHOOCHF 2OH
Ia1.645C(CH 3 ) 2HHOOCF 3OH
Ia1.646C(CH 3 ) 2CH 3HOSCH 3OH
Ia1.647C(CH 3 ) 2CH 3HOSCH 2 CH 3OH
Ia1.648C(CH 3 ) 2CH 3HOSO 2 CH 3OH
Ia1.649C(CH 3 ) 2CH 3HOSO 2 CH 2 CH 3OH
Ia1.650C(CH 3 ) 2CH 3HOSO 2 CH(CH 3 ) 2OH
Ia1.651C(CH 3 ) 2CH 3HOSO 2 (CH 2 ) 2 CH 3OH
Ia1.652C(CH 3 ) 2CH 3HOClOH
Ia1.653C(CH 3 ) 2CH 3HOBrOH
Ia1.654C(CH 3 ) 2CH 3HONO 2OH
Ia1.655C(CH 3 ) 2CH 3HOCHF 2OH
Ia1.656C(CH 3 ) 2CH 3HOCF 3OH
Ia1.657C(CH 3 ) 2CH 3HOOCH 3OH
Ia1.658C(CH 3 ) 2CH 3HOOCH 2 CH 3OH
Ia1.659C(CH 3 ) 2CH 3HOOCHF 2OH
Ia1.660C(CH 3 ) 2CH 3HOOCF 3OH
Ia1.661C(CH 3 ) 2CH 3CH 3OSCH 3OH
Ia1.662C(CH 3 ) 2CH 3CH 3OSCH 2 CH 3OH
Ia1.663C(CH 3 ) 2CH 3CH 3OSO 2 CH 3OH
Ia1.664C(CH 3 ) 2CH 3CH 3OSO 2 CH 2 CH 3OH
Ia1.665C(CH 3 ) 2CH 3CH 3OSO 2 CH(CH 3 ) 2OH
Ia1.666C(CH 3 ) 2CH 3CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ia1.667C(CH 3 ) 2CH 3CH 3OClOH
Ia1.668C(CH 3 ) 2CH 3CH 3OBrOH
Ia1.669C(CH 3 ) 2CH 3CH 3ONO 2OH
Ia1.670C(CH 3 ) 2CH 3CH 3OCHF 2OH
Ia1.671C(CH 3 ) 2CH 3CH 3OCF 3OH
Ia1.672C(CH 3 ) 2CH 3CH 3OOCH 3OH
Ia1.673C(CH 3 ) 2CH 3CH 3OOCH 2 CH 3OH
Ia1.674C(CH 3 ) 2CH 3CH 3OOCHF 2OH
Ia1.675C(CH 3 ) 2CH 3CH 3OOCF 3OH
Ia1.676C(CH 3 ) 2HHSSCH 3OH
Ia1.677C(CH 3 ) 2HHSSCH 2 CH 3OH
Ia1.678C(CH 3 ) 2HHSSO 2 CH 3OH
Ia1.679C(CH 3 ) 2HHSSO 2 CH 2 CH 3OH
Ia1.680C(CH 3 ) 2HHSSO 2 CH(CH 3 ) 2OH
Ia1.681C(CH 3 ) 2HHSSO 2 (CH 2 ) 2 CH 3OH
Ia1.682C(CH 3 ) 2HHSClOH
Ia1.683C(CH 3 ) 2HHSBrOH
Ia1.684C(CH 3 ) 2HHSNO 2OH
Ia1.685C(CH 3 ) 2HHSCHF 2OH
Ia1.686C(CH 3 ) 2HHSCF 3OH
Ia1.687C(CH 3 ) 2HHSOCH 3OH
Ia1.688C(CH 3 ) 2HHSOCH 2 CH 3OH
Ia1.689C(CH 3 ) 2HHSOCHF 2OH
Ia1.690C(CH 3 ) 2HHSOCF 3OH
Ia1.691C(CH 3 ) 2CH 3HSSCH 3OH
Ia1.692C(CH 3 ) 2CH 3HSSCH 2 CH 3OH
Ia1.693C(CH 3 ) 2CH 3HSSO 2 CH 3OH
Ia1.694C(CH 3 ) 2CH 3HSSO 2 CH 2 CH 3OH
Ia1.695C(CH 3 ) 2CH 3HSSO 2 CH(CH 3 ) 2OH
Ia1.696C(CH 3 ) 2CH 3HSSO 2 (CH 2 ) 2 CH 3OH
Ia1.697C(CH 3 ) 2CH 3HSClOH
Ia1.698C(CH 3 ) 2CH 3HSBrOH
Ia1.699C(CH 3 ) 2CH 3HSNO 2OH
Ia1.700C(CH 3 ) 2CH 3HSCHF 2OH
Ia1.701C(CH 3 ) 2CH 3HSCF 3OH
Ia1.702C(CH 3 ) 2CH 3HSOCH 3OH
Ia1.703C(CH 3 ) 2CH 3HSOCH 2 CH 3OH
Ia1.704C(CH 3 ) 2CH 3HSOCHF 2OH
Ia1.705C(CH 3 ) 2CH 3HSOCF 3OH
Ia1.706C(CH 3 ) 2CH 3CH 3SSCH 3OH
Ia1.707C(CH 3 ) 2CH 3CH 3SSCH 2 CH 3OH
Ia1.708C(CH 3 ) 2CH 3CH 3SSO 2 CH 3OH
Ia1.709C(CH 3 ) 2CH 3CH 3SSO 2 CH 2 CH 3OH
Ia1.710C(CH 3 ) 2CH 3CH 3SSO 2 CH(CH 3 ) 2OH
Ia1.711C(CH 3 ) 2CH 3CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ia1.712C(CH 3 ) 2CH 3CH 3SClOH
Ia1.713C(CH 3 ) 2CH 3CH 3SBrOH
Ia1.714C(CH 3 ) 2CH 3CH 3SNO 2OH
Ia1.715C(CH 3 ) 2CH 3CH 3SCHF 2OH
Ia1.716C(CH 3 ) 2CH 3CH 3SCF 3OH
Ia1.717C(CH 3 ) 2CH 3CH 3SOCH 3OH
Ia1.718C(CH 3 ) 2CH 3CH 3SOCH 2 CH 3OH
Ia1.719C(CH 3 ) 2CH 3CH 3SOCHF 2OH
Ia1.720C(CH 3 ) 2CH 3CH 3SOCF 3OH
Ia1.721C(CH 3 ) 2HHNCH 3SCH 3OH
Ia1.722C(CH 3 ) 2HHNCH 3SCH 2 CH 3OH
Ia1.723C(CH 3 ) 2HHNCH 3SO 2 CH 3OH
Ia1.724C(CH 3 ) 2HHNCH 3SO 2 CH 2 CH 3OH
Ia1.725C(CH 3 ) 2HHNCH 3SO 2 CH(CH 3 ) 2OH
Ia1.726C(CH 3 ) 2HHNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.727C(CH 3 ) 2HHNCH 3ClOH
Ia1.728C(CH 3 ) 2HHNCH 3BrOH
Ia1.729C(CH 3 ) 2HHNCH 3NO 2OH
Ia1.730C(CH 3 ) 2HHNCH 3CHF 2OH
Ia1.731C(CH 3 ) 2HHNCH 3CF 3OH
Ia1.732C(CH 3 ) 2HHNCH 3OCH 3OH
Ia1.733C(CH 3 ) 2HHNCH 3OCH 2 CH 3OH
Ia1.734C(CH 3 ) 2HHNCH 3OCHF 2OH
Ia1.735C(CH 3 ) 2HHNCH 3OCF 3OH
Ia1.736C(CH 3 ) 2CH 3HNCH 3SCH 3OH
Ia1.737C(CH 3 ) 2CH 3HNCH 3SCH 2 CH 3OH
Ia1.738C(CH 3 ) 2CH 3HNCH 3SO 2 CH 3OH
Ia1.739C(CH 3 ) 2CH 3HNCH 3SO 2 CH 2 CH 3OH
Ia1.740C(CH 3 ) 2CH 3HNCH 3SO 2 CH(CH 3 ) 2OH
Ia1.741C(CH 3 ) 2CH 3HNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.742C(CH 3 ) 2CH 3HNCH 3ClOH
Ia1.743C(CH 3 ) 2CH 3HNCH 3BrOH
Ia1.744C(CH 3 ) 2CH 3HNCH 3NO 2OH
Ia1.745C(CH 3 ) 2CH 3HNCH 3CHF 2OH
Ia1.746C(CH 3 ) 2CH 3HNCH 3CF 3OH
Ia1.747C(CH 3 ) 2CH 3HNCH 3OCH 3OH
Ia1.748C(CH 3 ) 2CH 3HNCH 3OCH 2 CH 3OH
Ia1.749C(CH 3 ) 2CH 3HNCH 3OCHF 2OH
Ia1.750C(CH 3 ) 2CH 3HNCH 3OCF 3OH
Ia1.751C(CH 3 ) 2CH 3CH 3NCH 3SCH 3OH
Ia1.752C(CH 3 ) 2CH 3CH 3NCH 3SCH 2 CH 3OH
Ia1.753C(CH 3 ) 2CH 3CH 3NCH 3SO 2 CH 3OH
Ia1.754C(CH 3 ) 2CH 3CH 3NCH 3SO 2 CH 2 CH 3OH
Ia1.755C(CH 3 ) 2CH 3CH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ia1.756C(CH 3 ) 2CH 3CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ia1.757C(CH 3 ) 2CH 3CH 3NCH 3ClOH
Ia1.758C(CH 3 ) 2CH 3CH 3NCH 3BrOH
Ia1.759C(CH 3 ) 2CH 3CH 3NCH 3NO 2OH
Ia1.760C(CH 3 ) 2CH 3CH 3NCH 3CHF 2OH
Ia1.761C(CH 3 ) 2CH 3CH 3NCH 3CF 3OH
Ia1.762C(CH 3 ) 2CH 3CH 3NCH 3OCH 3OH
Ia1.763C(CH 3 ) 2CH 3CH 3NCH 3OCH 2 CH 3OH
Ia1.764C(CH 3 ) 2CH 3CH 3NCH 3OCHF 2OH
Ia1.765C(CH 3 ) 2CH 3CH 3NCH 3OCF 3OH
TABLE 2
XR 2YR 4R 12
Ib1.1OHCHSCH 3OH
Ib1.2OHCHSCH 2 CH 3OH
Ib1.3OHCHSO 2 CH 3OH
Ib1.4OHCHSO 2 CH 2 CH 3OH
Ib1.5OHCHSO 2 CH(CH 3 ) 2OH
Ib1.6OHCHSO 2 (CH 2 ) 2 CH 3OH
Ib1.7OHCHClOH
Ib1.8OHCHBrOH
Ib1.9OHCHNO 2OH
Ib1.10OHCHCHF 2OH
Ib1.11OHCHCF 3OH
Ib1.12OHCHOCH 3OH
Ib1.13OHCHOCH 2 CH 3OH
Ib1.14OHCHOCHF 2OH
Ib1.15OHCHOCF 3OH
Ib1.16OCH 3CHSCH 3OH
Ib1.17OCH 3CHSCH 2 CH 3OH
Ib1.18OCH 3CHSO 2 CH 3OH
Ib1.19OCH 3CHSO 2 CH 2 CH 3OH
Ib1.20OCH 3CHSO 2 CH(CH 3 ) 2OH
Ib1.21OCH 3CHSO 2 (CH 2 ) 2 CH 3OH
Ib1.22OCH 3CHClOH
Ib1.23OCH 3CHBrOH
Ib1.24OCH 3CHNO 2OH
Ib1.25OCH 3CHCHF 2OH
Ib1.26OCH 3CHCF 3OH
Ib1.27OCH 3CHOCH 3OH
Ib1.28OCH 3CHOCH 2 CH 3OH
Ib1.29OCH 3CHOCHF 2OH
Ib1.30OCH 3CHOCF 3OH
Ib1.31OCH 2 CH 3CHSCH 3OH
Ib1.32OCH 2 CH 3CHSCH 2 CH 3OH
Ib1.33OCH 2 CH 3CHSO 2 CH 3OH
Ib1.34OCH 2 CH 3CHSO 2 CH 2 CH 3OH
Ib1.35OCH 2 CH 3CHSO 2 CH(CH 3 ) 2OH
Ib1.36OCH 2 CH 3CHSO 2 (CH 2 ) 2 CH 3OH
Ib1.37OCH 2 CH 3CHClOH
Ib1.38OCH 2 CH 3CHBrOH
Ib1.39OCH 2 CH 3CHNO 2OH
Ib1.40OCH 2 CH 3CHCHF 2OH
Ib1.41OCH 2 CH 3CHCF 3OH
Ib1.42OCH 2 CH 3CHOCH 3OH
Ib1.43OCH 2 CH 3CHOCH 2 CH 3OH
Ib1.44OCH 2 CH 3CHOCHF 2OH
Ib1.45OCH 2 CH 3CHOCF 3OH
Ib1.46OCH 2 ClCHSCH 3OH
Ib1.47OCH 2 ClCHSCH 2 CH 3OH
Ib1.48OCH 2 ClCHSO 2 CH 3OH
Ib1.49OCH 2 ClCHSO 2 CH 2 CH 3OH
Ib1.50OCH 2 ClCHSO 2 CH(CH 3 ) 2OH
Ib1.51OCH 2 ClCHSO 2 (CH 2 ) 2 CH 3OH
Ib1.52OCH 2 ClCHClOH
Ib1.53OCH 2 ClCHBrOH
Ib1.54OCH 2 ClCHNO 2OH
Ib1.55OCH 2 ClCHCHF 2OH
Ib1.56OCH 2 ClCHCF 3OH
Ib1.57OCH 2 ClCHOCH 3OH
Ib1.58OCH 2 ClCHOCH 2 CH 3OH
Ib1.59OCH 2 ClCHOCHF 2OH
Ib1.60OCH 2 ClCHOCF 3OH
Ib1.61OHC(CH 3 )SCH 3OH
Ib1.62OHC(CH 3 )SCH 2 CH 3OH
Ib1.63OHC(CH 3 )SO 2 CH 3OH
Ib1.64OHC(CH 3 )SO 2 CH 2 CH 3OH
Ib1.65OHC(CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.66OHC(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.67OHC(CH 3 )ClOH
Ib1.68OHC(CH 3 )BrOH
Ib1.69OHC(CH 3 )NO 2OH
Ib1.70OHC(CH 3 )CHF 2OH
Ib1.71OHC(CH 3 )CF 3OH
Ib1.72OHC(CH 3 )OCH 3OH
Ib1.73OHC(CH 3 )OCH 2 CH 3OH
Ib1.74OHC(CH 3 )OCHF 2OH
Ib1.75OHC(CH 3 )OCF 3OH
Ib1.76OCH 3C(CH 3 )SCH 3OH
Ib1.77OCH 3C(CH 3 )SCH 2 CH 3OH
Ib1.78OCH 3C(CH 3 )SO 2 CH 3OH
Ib1.79OCH 3C(CH 3 )SO 2 CH 2 CH 3OH
Ib1.80OCH 3C(CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.81OCH 3C(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.82OCH 3C(CH 3 )ClOH
Ib1.83OCH 3C(CH 3 )BrOH
Ib1.84OCH 3C(CH 3 )NO 2OH
Ib1.85OCH 3C(CH 3 )CHF 2OH
Ib1.86OCH 3C(CH 3 )CF 3OH
Ib1.87OCH 3C(CH 3 )OCH 3OH
Ib1.88OCH 3C(CH 3 )OCH 2 CH 3OH
Ib1.89OCH 3C(CH 3 )OCHF 2OH
Ib1.90OCH 3C(CH 3 )OCF 3OH
Ib1.91OCH 2 CH 3C(CH 3 )SCH 3OH
Ib1.92OCH 2 CH 3C(CH 3 )SCH 2 CH 3OH
Ib1.93OCH 2 CH 3C(CH 3 )SO 2 CH 3OH
Ib1.94OCH 2 CH 3C(CH 3 )SO 2 CH 2 CH 3OH
Ib1.95OCH 2 CH 3C(CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.96OCH 2 CH 3C(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.97OCH 2 CH 3C(CH 3 )ClOH
Ib1.98OCH 2 CH 3C(CH 3 )BrOH
Ib1.99OCH 2 CH 3C(CH 3 )NO 2OH
Ib1.100OCH 2 CH 3C(CH 3 )CHF 2OH
Ib1.101OCH 2 CH 3C(CH 3 )CF 3OH
Ib1.102OCH 2 CH 3C(CH 3 )OCH 3OH
Ib1.103OCH 2 CH 3C(CH 3 )OCH 2 CH 3OH
Ib1.104OCH 2 CH 3C(CH 3 )OCHF 2OH
Ib1.105OCH 2 CH 3C(CH 3 )OCF 3OH
Ib1.106OCH 2 ClC(CH 3 )SCH 3OH
Ib1.107OCH 2 ClC(CH 3 )SCH 2 CH 3OH
Ib1.108OCH 2 ClC(CH 3 )SO 2 CH 3OH
Ib1.109OCH 2 ClC(CH 3 )SO 2 CH 2 CH 3OH
Ib1.110OCH 2 ClC(CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.111OCH 2 ClC(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.112OCH 2 ClC(CH 3 )ClOH
Ib1.113OCH 2 ClC(CH 3 )BrOH
Ib1.114OCH 2 ClC(CH 3 )NO 2OH
Ib1.115OCH 2 ClC(CH 3 )CHF 2OH
Ib1.116OCH 2 ClC(CH 3 )CF 3OH
Ib1.117OCH 2 ClC(CH 3 )OCH 3OH
Ib1.118OCH 2 ClC(CH 3 )OCH 2 CH 3OH
Ib1.119OCH 2 ClC(CH 3 )OCHF 2OH
Ib1.120OCH 2 ClC(CH 3 )OCF 3OH
Ib1.121OHC(CH 2 CH 3 )SCH 3OH
Ib1.122OHC(CH 2 CH 3 )SCH 2 CH 3OH
Ib1.123OHC(CH 2 CH 3 )SO 2 CH 3OH
Ib1.124OHC(CH 2 CH 3 )SO 2 CH 2 CH 3OH
Ib1.125OHC(CH 2 CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.126OHC(CH 2 CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.127OHC(CH 2 CH 3 )ClOH
Ib1.128OHC(CH 2 CH 3 )BrOH
Ib1.129OHC(CH 2 CH 3 )NO 2OH
Ib1.130OHC(CH 2 CH 3 )CHF 2OH
Ib1.131OHC(CH 2 CH 3 )CF 3OH
Ib1.132OHC(CH 2 CH 3 )OCH 3OH
Ib1.133OHC(CH 2 CH 3 )OCH 2 CH 3OH
Ib1.134OHC(CH 2 CH 3 )OCHF 2OH
Ib1.135OHC(CH 2 CH 3 )OCF 3OH
Ib1.136OCH 3C(CH 2 CH 3 )SCH 3OH
Ib1.137OCH 3C(CH 2 CH 3 )SCH 2 CH 3OH
Ib1.138OCH 3C(CH 2 CH 3 )SO 2 CH 3OH
Ib1.139OCH 3C(CH 2 CH 3 )SO 2 CH 2 CH 3OH
Ib1.140OCH 3C(CH 2 CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.141OCH 3C(CH 2 CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.142OCH 3C(CH 2 CH 3 )ClOH
Ib1.143OCH 3C(CH 2 CH 3 )BrOH
Ib1.144OCH 3C(CH 2 CH 3 )NO 2OH
Ib1.145OCH 3C(CH 2 CH 3 )CHF 2OH
Ib1.146OCH 3C(CH 2 CH 3 )CF 3OH
Ib1.147OCH 3C(CH 2 CH 3 )OCH 3OH
Ib1.148OCH 3C(CH 2 CH 3 )OCH 2 CH 3OH
Ib1.149OCH 3C(CH 2 CH 3 )OCHF 2OH
Ib1.150OCH 3C(CH 2 CH 3 )OCF 3OH
Ib1.151OCH 2 CH 3C(CH 2 CH 3 )SCH 3OH
Ib1.152OCH 2 CH 3C(CH 2 CH 3 )SCH 2 CH 3OH
Ib1.153OCH 2 CH 3C(CH 2 CH 3 )SO 2 CH 3OH
Ib1.154OCH 2 CH 3C(CH 2 CH 3 )SO 2 CH 2 CH 3OH
Ib1.155OCH 2 CH 3C(CH 2 CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.156OCH 2 CH 3C(CH 2 CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.157OCH 2 CH 3C(CH 2 CH 3 )ClOH
Ib1.158OCH 2 CH 3C(CH 2 CH 3 )BrOH
Ib1.159OCH 2 CH 3C(CH 2 CH 3 )NO 2OH
Ib1.160OCH 2 CH 3C(CH 2 CH 3 )CHF 2OH
Ib1.161OCH 2 CH 3C(CH 2 CH 3 )CF 3OH
Ib1.162OCH 2 CH 3C(CH 2 CH 3 )OCH 3OH
Ib1.163OCH 2 CH 3C(CH 2 CH 3 )OCH 2 CH 3OH
Ib1.164OCH 2 CH 3C(CH 2 CH 3 )OCHF 2OH
Ib1.165OCH 2 CH 3C(CH 2 CH 3 )OCF 3OH
Ib1.166OCH 2 ClC(CH 2 CH 3 )SCH 3OH
Ib1.167OCH 2 ClC(CH 2 CH 3 )SCH 2 CH 3OH
Ib1.168OCH 2 ClC(CH 2 CH 3 )SO 2 CH 3OH
Ib1.169OCH 2 ClC(CH 2 CH 3 )SO 2 CH 2 CH 3OH
Ib1.170OCH 2 ClC(CH 2 CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.171OCH 2 ClC(CH 2 CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.172OCH 2 ClC(CH 2 CH 3 )ClOH
Ib1.173OCH 2 ClC(CH 2 CH 3 )BrOH
Ib1.174OCH 2 ClC(CH 2 CH 3 )NO 3OH
Ib1.175OCH 2 ClC(CH 2 CH 3 )CHF 2OH
Ib1.176OCH 2 ClC(CH 2 CH 3 )CF 3OH
Ib1.177OCH 2 ClC(CH 2 CH 3 )OCH 3OH
Ib1.178OCH 2 ClC(CH 2 CH 3 )OCH 2 CH 3OH
Ib1.179OCH 2 ClC(CH 2 CH 3 )OCHF 2OH
Ib1.180OCH 2 ClC(CH 2 CH 3 )OCF 3OH
Ib1.181NCH 3HCHSCH 3OH
Ib1.182NCH 3HCHSCH 2 CH 3OH
Ib1.183NCH 3HCHSO 2 CH 3OH
Ib1.184NCH 3HCHSO 2 CH 2 CH 3OH
Ib1.185NCH 3HCHSO 2 CH(CH 3 ) 2OH
Ib1.186NCH 3HCHSO 2 (CH 2 ) 2 CH 3OH
Ib1.187NCH 3HCHClOH
Ib1.188NCH 3HCHBrOH
Ib1.189NCH 3HCHNO 2OH
Ib1.190NCH 3HCHCHF 2OH
Ib1.191NCH 3HCHCF 3OH
Ib1.192NCH 3HCHOCH 3OH
Ib1.193NCH 3HCHOCH 2 CH 3OH
Ib1.194NCH 3HCHOCHF 2OH
Ib1.195NCH 3HCHOCF 3OH
Ib1.196NCH 3CH 3CHSCH 3OH
Ib1.197NCH 3CH 3CHSCH 2 CH 3OH
Ib1.198NCH 3CH 3CHSO 2 CH 3OH
Ib1.199NCH 3CH 3CHSO 2 CH 2 CH 3OH
Ib1.200NCH 3CH 3CHSO 2 CH(CH 3 ) 2OH
Ib1.201NCH 3CH 3CHSO 2 (CH 2 ) 2 CH 3OH
Ib1.202NCH 3CH 3CHClOH
Ib1.203NCH 3CH 3CHBrOH
Ib1.204NCH 3CH 3CHNO 2OH
Ib1.205NCH 3CH 3CHCHF 2OH
Ib1.206NCH 3CH 3CHCF 3OH
Ib1.207NCH 3CH 3CHOCH 3OH
Ib1.208NCH 3CH 3CHOCH 2 CH 3OH
Ib1.209NCH 3CH 3CHOCHF 2OH
Ib1.210NCH 3CH 3CHOCF 3OH
Ib1.211NCH 3CH 2 CH 3CHSCH 3OH
Ib1.212NCH 3CH 2 CH 3CHSCH 2 CH 3OH
Ib1.213NCH 3CH 2 CH 3CHSO 2 CH 3OH
Ib1.214NCH 3CH 2 CH 3CHSO 2 CH 2 CH 3OH
Ib1.215NCH 3CH 2 CH 3CHSO 2 CH(CH 3 ) 2OH
Ib1.216NCH 3CH 2 CH 3CHSO 2 (CH 2 ) 2 CH 3OH
Ib1.217NCH 3CH 2 CH 3CHClOH
Ib1.218NCH 3CH 2 CH 3CHBrOH
Ib1.219NCH 3CH 2 CH 3CHNO 2OH
Ib1.220NCH 3CH 2 CH 3CHCHF 2OH
Ib1.221NCH 3CH 2 CH 3CHCF 3OH
Ib1.222NCH 3CH 2 CH 3CHOCH 3OH
Ib1.223NCH 3CH 2 CH 3CHOCH 2 CH 3OH
Ib1.224NCH 3CH 2 CH 3CHOCHF 2OH
Ib1.225NCH 3CH 2 CH 3CHOCF 3OH
Ib1.226NCH 3CH 2 ClCHSCH 3OH
Ib1.227NCH 3CH 2 ClCHSCH 2 CH 3OH
Ib1.228NCH 3CH 2 ClCHSO 2 CH 3OH
Ib1.229NCH 3CH 2 ClCHSO 2 CH 2 CH 3OH
Ib1.230NCH 3CH 2 ClCHSO 2 CH(CH 3 ) 2OH
Ib1.231NCH 3CH 2 ClCHSO 2 (CH 2 ) 2 CH 3OH
Ib1.232NCH 3CH 2 ClCHClOH
Ib1.233NCH 3CH 2 ClCHBrOH
Ib1.234NCH 3CH 2 ClCHNO 2OH
Ib1.235NCH 3CH 2 ClCHCHF 2OH
Ib1.236NCH 3CH 2 ClCHCF 3OH
Ib1.237NCH 3CH 2 ClCHOCH 3OH
Ib1.238NCH 3CH 2 ClCHOCH 2 CH 3OH
Ib1.239NCH 3CH 2 ClCHOCHF 2OH
Ib1.240NCH 3CH 2 ClCHOCF 3OH
Ib1.241NCH 3HC(CH 3 )SCH 3OH
Ib1.242NCH 3HC(CH 3 )SCH 2 CH 3OH
Ib1.243NCH 3HC(CH 3 )SO 2 CH 3OH
Ib1.244NCH 3HC(CH 3 )SO 2 CH 2 CH 3OH
Ib1.245NCH 3HC(CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.246NCH 3HC(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.247NCH 3HC(CH 3 )ClOH
Ib1.248NCH 3HC(CH 3 )BrOH
Ib1.249NCH 3HC(CH 3 )NO 2OH
Ib1.250NCH 3HC(CH 3 )CHF 2OH
Ib1.251NCH 3HC(CH 3 )CF 3OH
Ib1.252NCH 3HC(CH 3 )OCH 3OH
Ib1.253NCH 3HC(CH 3 )OCH 2 CH 3OH
Ib1.254NCH 3HC(CH 3 )OCHF 2OH
Ib1.255NCH 3HC(CH 3 )OCF 3OH
Ib1.256NCH 3CH 3C(CH 3 )SCH 3OH
Ib1.257NCH 3CH 3C(CH 3 )SCH 2 CH 3OH
Ib1.258NCH 3CH 3C(CH 3 )SO 2 CH 3OH
Ib1.259NCH 3CH 3C(CH 3 )SO 2 CH 2 CH 3OH
Ib1.260NCH 3CH 3C(CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.261NCH 3CH 3C(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.262NCH 3CH 3C(CH 3 )ClOH
Ib1.263NCH 3CH 3C(CH 3 )BrOH
Ib1.264NCH 3CH 3C(CH 3 )NO 2OH
Ib1.265NCH 3CH 3C(CH 3 )CHF 2OH
Ib1.266NCH 3CH 3C(CH 3 )CF 3OH
Ib1.267NCH 3CH 3C(CH 3 )OCH 3OH
Ib1.268NCH 3CH 3C(CH 3 )OCH 2 CH 3OH
Ib1.269NCH 3CH 3C(CH 3 )OCHF 2OH
Ib1.270NCH 3CH 3C(CH 3 )OCF 3OH
Ib1.271NCH 3CH 2 CH 3C(CH 3 )SCH 3OH
Ib1.272NCH 3CH 2 CH 3C(CH 3 )SCH 2 CH 3OH
Ib1.273NCH 3CH 2 CH 3C(CH 3 )SO 2 CH 3OH
Ib1.274NCH 3CH 2 CH 3C(CH 3 )SO 2 CH 2 CH 3OH
Ib1.275NCH 3CH 2 CH 3C(CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.276NCH 3CH 2 CH 3C(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.277NCH 3CH 2 CH 3C(CH 3 )ClOH
Ib1.278NCH 3CH 2 CH 3C(CH 3 )BrOH
Ib1.279NCH 3CH 2 CH 3C(CH 3 )NO 2OH
Ib1.280NCH 3CH 2 CH 3C(CH 3 )CHF 2OH
Ib1.281NCH 3CH 2 CH 3C(CH 3 )CF 3OH
Ib1.282NCH 3CH 2 CH 3C(CH 3 )OCH 3OH
Ib1.283NCH 3CH 2 CH 3C(CH 3 )OCH 2 CH 3OH
Ib1.284NCH 3CH 2 CH 3C(CH 3 )OCHF 2OH
Ib1.285NCH 3CH 2 CH 3C(CH 3 )OCF 3OH
Ib1.286NCH 3CH 2 CH 3C(CH 3 )SCH 3OH
Ib1.287NCH 3CH 2 ClC(CH 3 )SCH 2 CH 3OH
Ib1.288NCH 3CH 2 ClC(CH 3 )SO 2 CH 3OH
Ib1.289NCH 3CH 2 ClC(CH 3 )SO 2 CH 2 CH 3OH
Ib1.290NCH 3CH 2 ClC(CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.291NCH 3CH 2 ClC(CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.292NCH 3CH 2 ClC(CH 3 )ClOH
Ib1.293NCH 3CH 2 ClC(CH 3 )BrOH
Ib1.294NCH 3CH 2 ClC(CH 3 )NO 2OH
Ib1.295NCH 3CH 2 ClC(CH 3 )CHF 2OH
Ib1.296NCH 3CH 2 ClC(CH 3 )CF 3OH
Ib1.297NCH 3CH 2 ClC(CH 3 )OCH 3OH
Ib1.298NCH 3CH 2 ClC(CH 3 )OCH 2 CH 3OH
Ib1.299NCH 3CH 2 ClC(CH 3 )OCHF 2OH
Ib1.300NCH 3CH 2 ClC(CH 3 )OCF 3OH
Ib1.301NCH 3HC(CH 2 CH 3 )SCH 3OH
Ib1.302NCH 3HC(CH 2 CH 3 )SCH 2 CH 3OH
Ib1.303NCH 3HC(CH 2 CH 3 )SO 2 CH 3OH
Ib1.304NCH 3HC(CH 2 CH 3 )SO 2 CH 2 CH 3OH
Ib1.305NCH 3HC(CH 2 CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.306NCH 3HC(CH 2 CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.307NCH 3HC(CH 2 CH 3 )ClOH
Ib1.308NCH 3HC(CH 2 CH 3 )BrOH
Ib1.309NCH 3HC(CH 2 CH 3 )NO 2OH
Ib1.310NCH 3HC(CH 2 CH 3 )CHF 2OH
Ib1.311NCH 3HC(CH 2 CH 3 )CF 3OH
Ib1.312NCH 3HC(CH 2 CH 3 )OCH 3OH
Ib1.313NCH 3HC(CH 2 CH 3 )OCH 2 CH 3OH
Ib1.314NCH 3HC(CH 2 CH 3 )OCHF 2OH
Ib1.315NCH 3HC(CH 2 CH 3 )OCF 3OH
Ib1.316NCH 3CH 3C(CH 2 CH 3 )SCH 3OH
Ib1.317NCH 3CH 3C(CH 2 CH 3 )SCH 2 CH 3OH
Ib1.318NCH 3CH 3C(CH 2 CH 3 )SO 2 CH 3OH
Ib1.319NCH 3CH 3C(CH 2 CH 3 )SO 2 CH 2 CH 3OH
Ib1.320NCH 3CH 3C(CH 2 CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.321NCH 3CH 3C(CH 2 CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.322NCH 3CH 3C(CH 2 CH 3 )ClOH
Ib1.323NCH 3CH 3C(CH 2 CH 3 )BrOH
Ib1.324NCH 3CH 3C(CH 2 CH 3 )NO 2OH
Ib1.325NCH 3CH 3C(CH 2 CH 3 )CHF 2OH
Ib1.326NCH 3CH 3C(CH 2 CH 3 )CF 3OH
Ib1.327NCH 3CH 3C(CH 2 CH 3 )OCH 3OH
Ib1.329NCH 3CH 3C(CH 2 CH 3 )OCH 2 CH 3OH
Ib1.329NCH 3CH 3C(CH 2 CH 3 )OCHF 2OH
Ib1.330NCH 3CH 3C(CH 2 CH 3 )OCF 3OH
Ib1.331NCH 3CH 2 CH 3C(CH 2 CH 3 )SCH 3OH
Ib1.332NCH 3CH 2 CH 3C(CH 2 CH 3 )SCH 2 CH 3OH
Ib1.333NCH 3CH 2 CH 3C(CH 2 CH 3 )SO 2 CH 3OH
Ib1.334NCH 3CH 2 CH 3C(CH 2 CH 3 )SO 2 CH 2 CH 3OH
Ib1.335NCH 3CH 2 CH 3C(CH 2 CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.336NCH 3CH 2 CH 3C(CH 2 CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.337NCH 3CH 2 CH 3C(CH 2 CH 3 )ClOH
Ib1.338NCH 3CH 2 CH 3C(CH 2 CH 3 )BrOH
Ib1.339NCH 3CH 2 CH 3C(CH 2 CH 3 )NO 2OH
Ib1.340NCH 3CH 2 CH 3C(CH 2 CH 3 )CHF 2OH
Ib1.341NCH 3CH 2 CH 3C(CH 2 CH 3 )CF 3OH
Ib1.342NCH 3CH 2 CH 3C(CH 2 CH 3 )OCH 3OH
Ib1.343NCH 3CH 2 CH 3C(CH 2 CH 3 )OCH 2 CH 3OH
Ib1.344NCH 3CH 2 CH 3C(CH 2 CH 3 )OCHF 2OH
Ib1.345NCH 3CH 2 CH 3C(CH 2 CH 3 )OCF 3OH
Ib1.346NCH 3CH 2 ClC(CH 2 CH 3 )SCH 3OH
Ib1.347NCH 3CH 2 ClC(CH 2 CH 3 )SCH 2 CH 3OH
Ib1.348NCH 3CH 2 ClC(CH 2 CH 3 )SO 2 CH 3OH
Ib1.349NCH 3CH 2 ClC(CH 2 CH 3 )SO 2 CH 2 CH 3OH
Ib1.350NCH 3CH 2 ClC(CH 2 CH 3 )SO 2 CH(CH 3 ) 2OH
Ib1.351NCH 3CH 2 ClC(CH 2 CH 3 )SO 2 (CH 2 ) 2 CH 3OH
Ib1.352NCH 3CH 2 ClC(CH 2 CH 3 )ClOH
Ib1.353NCH 3CH 2 ClC(CH 2 CH 3 )BrOH
Ib1.354NCH 3CH 2 ClC(CH 2 CH 3 )NO 2OH
Ib1.355NCH 3CH 2 ClC(CH 2 CH 3 )CHF 2OH
Ib1.356NCH 3CH 2 ClC(CH 2 CH 3 )CF 3OH
Ib1.357NCH 3CH 2 ClC(CH 2 CH 3 )OCH 3OH
Ib1.358NCH 3CH 2 ClC(CH 2 CH 3 )OCH 2 CH 3OH
Ib1.359NCH 3CH 2 ClC(CH 2 CH 3 )OCHF 2OH
Ib1.360NCH 3CH 2 ClC(CH 2 CH 3 )OCF 3OH
Ib1.361NCH 3HNSCH 3OH
Ib1.362NCH 3HNSCH 2 CH 3OH
Ib1.363NCH 3HNSO 2 CH 3OH
Ib1.364NCH 3HNSO 2 CH 2 CH 3OH
Ib1.365NCH 3HNSO 2 CH(CH 3 ) 2OH
Ib1.366NCH 3HNSO 2 (CH 2 ) 2 CH 3OH
Ib1.367NCH 3HNClOH
Ib1.368NCH 3HNBrOH
Ib1.369NCH 3HNNO 2OH
Ib1.370NCH 3HNCHF 2OH
Ib1.371NCH 3HNCF 3OH
Ib1.372NCH 3HNOCH 3OH
Ib1.373NCH 3HNOCH 2 CH 3OH
Ib1.374NCH 3HNOCHF 2OH
Ib1.375NCH 3HNOCF 3OH
Ib1.376NCH 3CH 3NSCH 3OH
Ib1.377NCH 3CH 3NSCH 2 CH 3OH
Ib1.378NCH 3CH 3NSO 2 CH 3OH
Ib1.379NCH 3CH 3NSO 2 CH 2 CH 3OH
Ib1.380NCH 3CH 3NSO 2 CH(CH 3 ) 2OH
Ib1.381NCH 3CH 3NSO 2 (CH 2 ) 2 CH 3OH
Ib1.382NCH 3CH 3NClOH
Ib1.383NCH 3CH 3NBrOH
Ib1.384NCH 3CH 3NNO 2OH
Ib1.385NCH 3CH 3NCHF 2OH
Ib1.386NCH 3CH 3NCF 3OH
Ib1.387NCH 3CH 3NOCH 3OH
Ib1.388NCH 3CH 3NOCH 2 CH 3OH
Ib1.389NCH 3CH 3NOCHF 2OH
Ib1.390NCH 3CH 3NOCF 3OH
Ib1.391NCH 3CH 2 CH 3NSCH 3OH
Ib1.392NCH 3CH 2 CH 3NSCH 2 CH 3OH
Ib1.393NCH 3CH 2 CH 3NSO 2 CH 3OH
Ib1.394NCH 3CH 2 CH 3NSO 2 CH 2 CH 3OH
Ib1.395NCH 3CH 2 CH 3NSO 2 CH(CH 3 ) 2OH
Ib1.396NCH 3CH 2 CH 3NSO 2 (CH 2 ) 2 CH 3OH
Ib1.397NCH 3CH 2 CH 3NClOH
Ib1.398NCH 3CH 2 CH 3NBrOH
Ib1.399NCH 3CH 2 CH 3NNO 3OH
Ib1.400NCH 3CH 2 CH 3NCHF 2OH
Ib1.401NCH 3CH 2 CH 3NCF 3OH
Ib1.402NCH 3CH 2 CH 3NOCH 3OH
Ib1.403NCH 3CH 2 CH 3NOCH 2 CH 3OH
Ib1.404NCH 3CH 2 CH 3NOCHF 2OH
Ib1.405NCH 3CH 2 CH 3NOCF 3OH
Ib1.406NCH 3CH 2 ClNSCH 3OH
Ib1.407NCH 3CH 2 ClNSCH 2 CH 3OH
Ib1.408NCH 3CH 2 ClNSO 2 CH 3OH
Ib1.409NCH 3CH 2 ClNSO 2 CH 2 CH 3OH
Ib1.410NCH 3CH 2 ClNSO 2 CH(CH 3 ) 2OH
Ib1.411NCH 3CH 2 ClNSO 2 (CH 2 ) 2 CH 3OH
Ib1.412NCH 3CH 2 ClNClOH
Ib1.413NCH 3CH 2 ClNBrOH
Ib1.414NCH 3CH 2 ClNNO 2OH
Ib1.415NCH 3CH 2 ClNCHF 2OH
Ib1.416NCH 3CH 2 ClNCF 3OH
Ib1.417NCH 3CH 2 ClNOCH 3OH
Ib1.418NCH 3CH 2 ClNOCH 2 CH 3OH
Ib1.419NCH 3CH 2 ClNOCHF 2OH
Ib1.420NCH 3CH 2 ClNOCF 3OH
TABLE 3
No.XR 2YR 4R 8
Ic1.1CHHOSCH 3OH
Ic1.2CHHOSCH 2 CH 3OH
Ic1.3CHHOSO 2 CH 3OH
Ic1.4CHHOSO 2 CH 2 CH 3OH
Ic1.5CHHOSO 2 CH(CH 3 ) 2OH
Ic1.6CHHOSO 2 (CH 2 ) 2 CH 3OH
Ic1.7CHHOClOH
Ic1.8CHHOBrOH
Ic1.9CHHONO 2OH
Ic1.10CHHOCHF 2OH
Ic1.11CHHOCF 3OH
Ic1.12CHHOOCH 3OH
Ic1.13CHHOOCH 2 CH 3OH
Ic1.14CHHOOCHF 2OH
Ic1.15CHHOOCF 3OH
Ic1.16CHCH 3OSCH 3OH
Ic1.17CHCH 3OSCH 2 CH 3OH
Ic1.18CHCH 3OSO 2 CH 3OH
Ic1.19CHCH 3OSO 2 CH 2 CH 3OH
Ic1.20CHCH 3OSO 2 CH(CH 3 ) 2OH
Ic1.21CHCH 3OSO 2 (CH 2 ) 2 CH 3OH
Ic1.22CHCH 3OClOH
Ic1.23CHCH 3OBrOH
Ic1.24CHCH 3ONO 2OH
Ic1.25CHCH 3OCHF 2OH
Ic1.26CHCH 3OCF 3OH
Ic1.27CHCH 3OOCH 3OH
Ic1.28CHCH 3OOCH 2 CH 3OH
Ic1.29CHCH 3OOCF 2OH
Ic1.30CHCH 3OOCF 3OM
Ic1.31CHCH 2 CH 3OSCH 3OH
Ic1.32CHCH 2 CH 3OSCH 2 CH 3OH
Ic1.33CHCH 2 CH 3OSO 2 CH 3OH
Ic1.34CHCH 2 CH 3OSO 2 CH 2 CH 3OH
Ic1.35CHCH 2 CH 3OSO 2 CH(CH 3 ) 3OH
Ic1.36CHCH 2 CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ic1.37CHCH 2 CH 3OClOH
Ic1.38CHCH 2 CH 3OBrOH
Ic1.39CHCH 2 CH 3ONO 2OH
Ic1.40CHCH 2 CH 3OCHF 2OH
Ic1.41CHCH 2 CH 3OCF 3OH
Ic1.42CHCH 2 CH 3OOCH 3OH
Ic1.43CHCH 2 CH 3OOCH 2 CH 3OH
Ic1.44CHCH 2 CH 3OOCHF 2OH
Ic1.45CHCH 2 CH 3OOCF 3OH
Ic1.46CHCH 2 ClOSCH 3OH
Ic1.47CHCH 2 ClOSCH 2 CH 3OH
Ic1.48CHCH 2 ClOSO 2 CH 3OH
Ic1.49CHCH 2 ClOSO 2 CH 2 CH 3OH
Ic1.50CHCH 2 ClOSO 2 CH(CH 3 ) 2OH
Ic1.51CHCH 2 ClOSO 2 (CH 2 ) 2 CH 3OH
Ic1.52CHCH 2 ClOClOH
Ic1.53CHCH 2 ClOBrOH
Ic1.54CHCH 2 ClONO 2OH
Ic1.55CHCH 2 ClOCHF 2OH
Ic1.56CHCH 2 ClOCF 3OH
Ic1.57CHCH 2 ClOOCH 3OH
Ic1.58CHCH 2 ClOOCH 2 CH 3OH
Ic1.59CHCH 2 ClOOCHF 2OH
Ic1.60CHCH 2 ClOOCF 3OH
Ic1.61CHHSSCH 3OH
Ic1.62CHHSSCH 2 CH 3OH
Ic1.63CHHSSO 2 CH 3OH
Ic1.64CHHSSO 2 CH 2 CH 3OH
Ic1.65CHHSSO 2 CH(CH 3 ) 2OH
Ic1.66CHHSSO 2 (CH 2 ) 2 CH 3OH
Ic1.67CHHSClOH
Ic1.68CHHSBrOH
Ic1.69CHHSNO 2OH
Ic1.70CHHSCHF 2OH
Ic1.71CHHSCF 3OH
Ic1.72CHHSOCH 3OH
Ic1.73CHHSOCH 2 CH 3OH
Ic1.74CHHSOCHF 2OH
Ic1.75CHHSOCF 3OH
Ic1.76CHCH 3SSCH 3OH
Ic1.77CHCH 3SSCH 2 CH 3OH
Ic1.78CHCH 3SSO 2 CH 3OH
Ic1.79CHCH 3SSO 2 CH 2 CH 3OH
Ic1.80CHCH 3SSO 2 CH(CH 3 ) 2OH
Ic1.81CHCH 3SSO 2 (CH 2 ) 2 CH 3OH
Ic1.82CHCH 3SClOH
Ic1.83CHCH 3SBrOH
Ic1.84CHCH 3SNO 2OH
Ic1.85CHCH 3SCHF 2OH
Ic1.86CHCH 3SCF 3OH
Ic1.87CHCH 3SOCH 3OH
Ic1.88CHCH 3SOCH 2 CH 3OH
Ic1.89CHCH 3SOCHF 2OH
Ic1.90CHCH 3SOCF 3OH
Ic1.91CHCH 2 CH 3SSCH 3OH
Ic1.92CHCH 2 CH 3SSCH 2 CH 3OH
Ic1.93CHCH 2 CH 3SSO 2 CH 3OH
Ic1.94CHCH 2 CH 3SSO 2 CH 2 CH 3OH
Ic1.95CHCH 2 CH 3SSO 2 CH(CH 3 ) 2OH
Ic1.96CHCH 2 CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ic1.97CHCH 2 CH 3SClOH
Ic1.98CHCH 2 CH 3SBrOH
Ic1.99CHCH 2 CH 3SNO 2OH
Ic1.100CHCH 2 CH 3SCHF 2OH
Ic1.101CHCH 2 CH 3SCF 3OH
Ic1.102CHCH 2 CH 3SOCH 3OH
Ic1.103CHCH 2 CH 3SOCH 2 CH 3OH
Ic1.104CHCH 2 CH 3SOCHF 2OH
Ic1.105CHCH 2 CH 3SOCF 3OH
Ic1.106CHCH 2 ClSSCH 3OH
Ic1.107CHCH 2 ClSSCH 2 CH 3OH
Ic1.108CHCH 2 ClSSO 2 CH 3OH
Ic1.109CHCH 2 ClSSO 2 CH 2 CH 3OH
Ic1.110CHCH 2 ClSSO 2 CH(CH 3 ) 2OH
Ic1.111CHCH 2 ClSSO 2 (CH 2 ) 2 CH 3OH
Ic1.112CHCH 2 ClSClOH
Ic1.113CHCH 2 ClSBrOH
Ic1.114CHCH 2 ClSNO 2OH
Ic1.115CHCH 2 ClSCHF 2OH
Ic1.116CHCH 2 ClSCF 3OH
Ic1.117CHCH 2 ClSOCH 3OH
Ic1.118CHCH 2 ClSOCH 2 CH 3OH
Ic1.119CHCH 2 ClSOCHF 2OH
Ic1.120CHCH 2 ClSOCF 3OH
Ic1.121CHHNCH 3SCH 3OH
Ic1.122CHHNCH 3SCH 2 CH 3OH
Ic1.123CHHNCH 3SO 2 CH 3OH
Ic1.124CHHNCH 3SO 2 CH 2 CH 3OH
Ic1.125CHHNCH 3SO 2 CH(CH 3 ) 2OH
Ic1.126CHHNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.127CHHNCH 3ClOH
Ic1.128CHHNCH 3BrOH
Ic1.129CHHNCH 3NO 2OH
Ic1.130CHHNCH 3CHF 2OH
Ic1.131CHHNCH 3CF 3OH
Ic1.132CHHNCH 3OCH 3OH
Ic1.133CHHNCH 3OCH 2 CH 3OH
Ic1.134CHHNCH 3OCHF 2OH
Ic1.135CHHNCH 3OCF 3OH
Ic1.136CHCH 3NCH 3SCH 3OH
Ic1.137CHCH 3NCH 3SCH 2 CH 3OH
Ic1.138CHCH 3NCH 3SO 2 CH 3OH
Ic1.139CHCH 3NCH 3SO 2 CH 2 CH 3OH
Ic1.140CHCH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ic1.141CHCH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.142CHCH 3NCH 3ClOH
Ic1.143CHCH 3NCH 3BrOH
Ic1.144CHCH 3NCH 3NO 2OH
Ic1.145CHCH 3NCH 3CHF 2OH
Ic1.146CHCH 3NCH 3CF 3OH
Ic1.147CHCH 3NCH 3OCH 3OH
Ic1.148CHCH 3NCH 3OCH 2 CH 3OH
Ic1.149CHCH 3NCH 3OCHF 2OH
Ic1.150CHCH 3NCH 3OCF 3OH
Ic1.151CHCH 2 CH 3NCH 3SCH 3OH
Ic1.152CHCH 2 CH 3NCH 3SCH 2 CH 3OH
Ic1.153CHCH 2 CH 3NCH 3SO 2 CH 3OH
Ic1.154CHCH 2 CH 3NCH 3SO 2 CH 2 CH 3OH
Ic1.155CHCH 2 CH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ic1.156CHCH 2 CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.157CHCH 2 CH 3NCH 3ClOH
Ic1.158CHCH 2 CH 3NCH 3BrOH
Ic1.159CHCH 2 CH 3NCH 3NO 2OH
Ic1.160CHCH 2 CH 3NCH 3CHF 2OH
Ic1.161CHCH 2 CH 3NCH 3CF 3OH
Ic1.162CHCH 2 CH 3NCH 3OCH 3OH
Ic1.163CHCH 2 CH 3NCH 3OCH 2 CH 3OH
Ic1.164CHCH 2 CH 3NCH 3OCHF 2OH
Ic1.165CHCH 2 CH 3NCH 3OCF 3OH
Ic1.166CHCH 2 ClNCH 3SCH 3OH
Ic1.167CHCH 2 ClNCH 3SCH 2 CH 3OH
Ic1.168CHCH 2 ClNCH 3SO 2 CH 3OH
Ic1.169CHCH 2 ClNCH 3SO 2 CH 2 CH 3OH
Ic1.170CHCH 2 ClNCH 3SO 2 CH(CH 3 ) 2OH
Ic1.171CHCH 2 ClNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.172CHCH 2 ClNCH 3ClOH
Ic1.173CHCH 2 ClNCH 3BrOH
Ic1.174CHCH 2 ClNCH 3NO 2OH
Ic1.175CHCH 2 ClNCH 3CHF 2OH
Ic1.176CHCH 2 ClNCH 3CF 3OH
Ic1.177CHCH 2 ClNCH 3OCH 3OH
Ic1.178CHCH 2 ClNCH 3OCH 2 CH 3OH
Ic1.179CHCH 2 ClNCH 3OCHF 2OH
Ic1.180CHCH 2 ClNCH 3OCF 3OH
Ic1.181C(CH 3 )HOSCH 3OH
Ic1.182C(CH 3 )HOSCH 2 CH 3OH
Ic1.183C(CH 3 )HOSO 2 CH 3OH
Ic1.184C(CH 3 )HOSO 2 CH 2 CH 3OH
Ic1.185C(CH 3 )HOSO 2 CH(CH 3 ) 2OH
Ic1.186C(CH 3 )HOSO 2 (CH 2 ) 2 CH 3OH
Ic1.187C(CH 3 )HOClOH
Ic1.188C(CH 3 )HOBrOH
Ic1.189C(CH 3 )HONO 2OH
Ic1.190C(CH 3 )HOCHF 2OH
Ic1.191C(CH 3 )HOCF 3OH
Ic1.192C(CH 3 )HOOCH 3OH
Ic1.193C(CH 3 )HOOCH 2 CH 3OH
Ic1.194C(CH 3 )HOOCHF 2OH
Ic1.195C(CH 3 )HOOCF 3OH
Ic1.196C(CH 3 )CH 3OSCH 3OH
Ic1.197C(CH 3 )CH 3OSCH 2 CH 3OH
Ic1.198C(CH 3 )CH 3OSO 2 CH 3OH
Ic1.199C(CH 3 )CH 3OSO 2 CH 2 CH 3OH
Ic1.200C(CH 3 )CH 3OSO 2 CH(CH 3 ) 2OH
Ic1.201C(CH 3 )CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ic1.202C(CH 3 )CH 3OClOH
Ic1.203C(CH 3 )CH 3OBrOH
Ic1.204C(CH 3 )CH 3ONO 2OH
Ic1.205C(CH 3 )CH 3OCHF 2OH
Ic1.206C(CH 3 )CH 3OCF 3OH
Ic1.207C(CH 3 )CH 3OOCH 3OH
Ic1.208C(CH 3 )CH 3OOCH 2 CH 3OH
Ic1.209C(CH 3 )CH 3OOCHF 2OH
Ic1.210C(CH 3 )CH 3OOCF 3OH
Ic1.211C(CH 3 )CH 2 CH 3OSCH 3OH
Ic1.212C(CH 3 )CH 2 CH 3OSCH 2 CH 3OH
Ic1.213C(CH 3 )CH 2 CH 3OSO 2 CH 3OH
Ic1.214C(CH 3 )CH 2 CH 3OSO 2 CH 2 CH 3OH
Ic1.215C(CH 3 )CH 2 CH 3OSO 2 CH(CH 3 ) 2OH
Ic1.216C(CH 3 )CH 2 CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ic1.217C(CH 3 )CH 2 CH 3OClOH
Ic1.218C(CH 3 )CH 2 CH 3OBrOH
Ic1.219C(CH 3 )CH 2 CH 3ONO 2OH
Ic1.220C(CH 3 )CH 2 CH 3OCHF 2OH
Ic1.221C(CH 3 )CH 2 CH 3OCF 3OH
Ic1.222C(CH 3 )CH 2 CH 3OOCH 3OH
Ic1.223C(CH 3 )CH 2 CH 3OOCH 2 CH 3OH
Ic1.224C(CH 3 )CH 2 CH 3OOCHF 2OH
Ic1.225C(CH 3 )CH 2 CH 3OOCF 3OH
Ic1.226C(CH 3 )CH 2 ClOSCH 3OH
Ic1.227C(CH 3 )CH 2 ClOSCH 2 CH 3OH
Ic1.228C(CH 3 )CH 2 ClOSO 2 CH 3OH
Ic1.229C(CH 3 )CH 2 ClOSO 2 CH 2 CH 3OH
Ic1.230C(CH 3 )CH 2 ClOSO 2 CH(CH 3 ) 2OH
Ic1.231C(CH 3 )CH 2 ClOSO 2 (CH 2 ) 2 CH 3OH
Ic1.232C(CH 3 )CH 2 ClOClOH
Ic1.233C(CH 3 )CH 2 ClOBrOH
Ic1.234C(CH 3 )CH 2 ClONO 2OH
Ic1.235C(CH 3 )CH 2 ClOCHF 2OH
Ic1.236C(CH 3 )CH 2 ClOCF 3OH
Ic1.237C(CH 3 )CH 2 ClOOCH 3OH
Ic1.238C(CH 3 )CH 2 ClOOCH 2 CH 3OH
Ic1.239C(CH 3 )CH 2 ClOOCHF 2OH
Ic1.240C(CH 3 )CH 2 ClOOCF 3OH
Ic1.241C(CH 3 )HSSCH 3OH
Ic1.242C(CH 3 )HSSCH 2 CH 3OH
Ic1.243C(CH 3 )HSSO 2 CH 3OH
Ic1.244C(CH 3 )HSSO 2 CH 2 CH 3OH
Ic1.245C(CH 3 )HSSO 2 CH(CH 3 ) 2OH
Ic1.246C(CH 3 )HSSO 2 (CH 2 ) 2 CH 3OH
Ic1.247C(CH 3 )HSClOH
Ic1.248C(CH 3 )HSBrOH
Ic1.249C(CH 3 )HSNO 2OH
Ic1.250C(CH 3 )HSCHF 2OH
Ic1.251C(CH 3 )HSCF 3OH
Ic1.252C(CH 3 )HSOCH 3OH
Ic1.253C(CH 3 )HSOCH 2 CH 3OH
Ic1.254C(CH 3 )HSOCHF 2OH
Ic1.255C(CH 3 )HSOCF 3OH
Ic1.256C(CH 3 )CH 3SSCH 3OH
Ic1.257C(CH 3 )CH 3SSCH 2 CH 3OH
Ic1.258C(CH 3 )CH 3SSO 2 CH 3OH
Ic1.259C(CH 3 )CH 3SSO 2 CH 2 CH 3OH
Ic1.260C(CH 3 )CH 3SSO 2 CH(CH 3 ) 2OH
Ic1.261C(CH 3 )CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ic1.262C(CH 3 )CH 3SClOH
Ic1.263C(CH 3 )CH 3SBrOH
Ic1.264C(CH 3 )CH 3SNO 2OH
Ic1.265C(CH 3 )CH 3SCHF 3OH
Ic1.266C(CH 3 )CH 3SCF 3OH
Ic1.267C(CH 3 )CH 3SOCH 3OH
Ic1.268C(CH 3 )CH 3SOCH 2 CH 3OH
Ic1.269C(CH 3 )CH 3SOCHF 2OH
Ic1.270C(CH 3 )CH 3SOCF 3OH
Ic1.271C(CH 3 )CH 2 CH 3SSCH 3OH
Ic1.272C(CH 3 )CH 2 CH 3SSCH 2 CH 3OH
Ic1.273C(CH 3 )CH 2 CH 3SSO 2 CH 3OH
Ic1.274C(CH 3 )CH 2 CH 3SSO 2 CH 2 CH 3OH
Ic1.275C(CH 3 )CH 2 CH 3SSO 2 CH(CH 3 ) 2OH
Ic1.276C(CH 3 )CH 2 CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ic1.277C(CH 3 )CH 2 CH 3SClOH
Ic1.278C(CH 3 )CH 2 CH 3SBrOH
Ic1.279C(CH 3 )CH 2 CH 3SNO 2OH
Ic1.280C(CH 3 )CH 2 CH 3SCHF 2OH
Ic1.281C(CH 3 )CH 2 CH 3SCF 3OH
Ic1.282C(CH 3 )CH 2 CH 3SOCH 3OH
Ic1.283C(CH 3 )CH 2 CH 3SOCH 2 CH 3OH
Ic1.284C(CH 3 )CH 2 CH 3SOCHF 2OH
Ic1.285C(CH 3 )CH 2 CH 3SOCF 3OH
Ic1.286C(CH 3 )CH 2 ClSSCH 3OH
Ic1.287C(CH 3 )CH 2 ClSSCH 2 CH 3OH
Ic1.288C(CH 3 )CH 2 ClSSO 2 CH 3OH
Ic1.289C(CH 3 )CH 2 ClSSO 2 CH 2 CH 3OH
Ic1.290C(CH 3 )CH 2 ClSSO 2 CH(CH 3 ) 2OH
Ic1.291C(CH 3 )CH 2 ClSSO 2 (CH 2 ) 2 CH 3OH
Ic1.292C(CH 3 )CH 2 ClSClOH
Ic1.293C(CH 3 )CH 2 ClSBrOH
Ic1.294C(CH 3 )CH 2 ClSNO 2OH
Ic1.295C(CH 3 )CH 2 ClSCHF 2OH
Ic1.296C(CH 3 )CH 2 ClSCF 3OH
Ic1.297C(CH 3 )CH 2 ClSOCH 3OH
Ic1.298C(CH 3 )CH 2 ClSOCH 2 CH 3OH
Ic1.299C(CH 3 )CH 2 ClSOCHF 2OH
Ic1.300C(CH 3 )CH 2 ClSOCF 3OH
Ic1.301C(CH 3 )HNCH 3SCH 3OH
Ic1.302C(CH 3 )HNCH 3SCH 2 CH 3OH
Ic1.303C(CH 3 )HNCH 3SO 2 CH 3OH
Ic1.304C(CH 3 )HNCH 3SO 2 CH 2 CH 3OH
Ic1.305C(CH 3 )HNCH 3SO 2 CH(CH 3 ) 2OH
Ic1.306C(CH 3 )HNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.307C(CH 3 )HNCH 3ClOH
Ic1.308C(CH 3 )HNCH 3BrOH
Ic1.309C(CH 3 )HNCH 3NO 2OH
Ic1.310C(CH 3 )HNCH 3CHF 2OH
Ic1.311C(CH 3 )HNCH 3CF 3OH
Ic1.312C(CH 3 )HNCH 3OCH 3OH
Ic1.313C(CH 3 )HNCH 3OCH 2 CH 3OH
Ic1.314C(CH 3 )HNCH 3OCHF 2OH
Ic1.315C(CH 3 )HNCH 3OCF 3OH
Ic1.316C(CH 3 )CH 3NCH 3SCH 3OH
Ic1.317C(CH 3 )CH 3NCH 3SCH 2 CH 3OH
Ic1.318C(CH 3 )CH 3NCH 3SO 2 CH 3OH
Ic1.319C(CH 3 )CH 3NCH 3SO 2 CH 2 CH 3OH
Ic1.320C(CH 3 )CH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ic1.321C(CH 3 )CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.322C(CH 3 )CH 3NCH 3ClOH
Ic1.323C(CH 3 )CH 3NCH 3BrOH
Ic1.324C(CH 3 )CH 3NCH 3NO 2OH
Ic1.325C(CH 3 )CH 3NCH 3CHF 2OH
Ic1.326C(CH 3 )CH 3NCH 3CF 3OH
Ic1.327C(CH 3 )CH 3NCH 3OCH 3OH
Ic1.328C(CH 3 )CH 3NCH 3OCH 2 CH 3OH
Ic1.329C(CH 3 )CH 3NCH 3OCHF 2OH
Ic1.330C(CH 3 )CH 3NCH 3OCF 3OH
Ic1.331C(CH 3 )CH 2 CH 3NCH 3SCH 3OH
Ic1.332C(CH 3 )CH 2 CH 3NCH 3SCH 2 CH 3OH
Ic1.333C(CH 3 )CH 2 CH 3NCH 3SO 2 CH 2OH
Ic1.334C(CH 3 )CH 2 CH 3NCH 3SO 2 CH 2 CH 3OH
Ic1.335C(CH 3 )CH 2 CH 3NCH 3SO 2 CH(CH 2 ) 2OH
Ic1.336C(CH 3 )CH 2 CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.337C(CH 3 )CH 2 CH 3NCH 3ClOH
Ic1.338C(CH 3 )CH 2 CH 3NCH 3BrOH
Ic1.339C(CH 3 )CH 2 CH 3NCH 3NO 2OH
Ic1.340C(CH 3 )CH 2 CH 3NCH 3CHF 2OH
Ic1.341C(CH 3 )CH 2 CH 3NCH 3CF 3OH
Ic1.342C(CH 3 )CH 2 CH 3NCH 3OCH 3OH
Ic1.343C(CH 3 )CH 2 CH 3NCH 3OCH 2 CH 3OH
Ic1.344C(CH 3 )CH 2 CH 3NCH 3OCHF 2OH
Ic1.345C(CH 3 )CH 2 CH 3NCH 3OCF 3OH
Ic1.346C(CH 3 )CH 2 ClNCH 3SCH 3OH
Ic1.347C(CH 3 )CH 2 ClNCH 3SCH 2 CH 3OH
Ic1.348C(CH 3 )CH 2 ClNCH 3SO 2 CH 3OH
Ic1.349C(CH 3 )CH 2 ClNCH 3SO 2 CH 2 CH 3OH
Ic1.350C(CH 3 )CH 2 ClNCH 3SO 2 CH(CH 3 ) 2OH
Ic1.351C(CH 3 )CH 2 ClNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.352C(CH 3 )CH 2 ClNCH 3ClOH
Ic1.353C(CH 3 )CH 2 ClNCH 3BrOH
Ic1.354C(CH 3 )CH 2 ClNCH 3NO 2OH
Ic1.355C(CH 3 )CH 2 ClNCH 3CHF 2OH
Ic1.356C(CH 3 )CH 2 ClNCH 3CF 3OH
Ic1.357C(CH 3 )CH 2 ClNCH 3OCH 3OH
Ic1.358C(CH 3 )CH 2 ClNCH 3OCH 2 CH 3OH
Ic1.359C(CH 3 )CH 2 ClNCH 3OCHF 2OH
Ic1.360C(CH 3 )CH 2 ClNCH 3OCF 3OH
Ic1.361C(CH 2 CH 3 )HOSCH 3OH
Ic1.362C(CH 2 CH 3 )HOSCH 2 CH 3OH
Ic1.363C(CH 2 CH 3 )HOSO 2 CH 3OH
Ic1.364C(CH 2 CH 3 )HOSO 2 CH 2 CH 3OH
Ic1.365C(CH 2 CH 3 )HOSO 2 CH(CH 3 ) 2OH
Ic1.366C(CH 2 CH 3 )HOSO 2 (CH 2 ) 2 CH 3OH
Ic1.367C(CH 2 CH 3 )HOClOH
Ic1.368C(CH 2 CH 3 )HOBrOH
Ic1.369C(CH 2 CH 3 )HONO 2OH
Ic1.370C(CH 2 CH 3 )HOCHF 2OH
Ic1.371C(CH 2 CH 3 )HOCF 3OH
Ic1.372C(CH 2 CH 3 )HOOCH 3OH
Ic1.373C(CH 2 CH 3 )HOOCH 2 CH 3OH
Ic1.374C(CH 2 CH 3 )HOOCHF 2OH
Ic1.375C(CH 2 CH 3 )HOOCF 3OH
Ic1.376C(CH 2 CH 3 )CH 3OSCH 3OH
Ic1.377C(CH 2 CH 3 )CH 3OSCH 2 CH 3OH
Ic1.378C(CH 2 CH 3 )CH 3OSO 2 CH 3OH
Ic1.379C(CH 2 CH 3 )CH 3OSO 2 CH 2 CH 3OH
Ic1.380C(CH 2 CH 3 )CH 3OSO 2 CH(CH 3 ) 2OH
Ic1.381C(CH 2 CH 3 )CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ic1.382C(CH 2 CH 3 )CH 3OClOH
Ic1.383C(CH 2 CH 3 )CH 3OBrOH
Ic1.384C(CH 2 CH 3 )CH 3ONO 2OH
Ic1.385C(CH 2 CH 3 )CH 3OCHF 2OH
Ic1.386C(CH 2 CH 3 )CH 3OCF 3OH
Ic1.387C(CH 2 CH 3 )CH 3OOCH 3OH
Ic1.388C(CH 2 CH 3 )CH 3OOCH 2 CH 3OH
Ic1.389C(CH 2 CH 3 )CH 3OOCHF 2OH
Ic1.390C(CH 2 CH 3 )CH 3OOCF 3OH
Ic1.391C(CH 2 CH 3 )CH 2 CH 3OSCH 3OH
Ic1.392C(CH 2 CH 3 )CH 2 CH 3OSCH 2 CH 3OH
Ic1.393C(CH 2 CH 3 )CH 2 CH 3OSO 2 CH 3OH
Ic1.394C(CH 2 CH 3 )CH 2 CH 3OSO 2 CH 2 CH 3OH
Ic1.395C(CH 2 CH 3 )CH 2 CH 3OSO 2 CH(CH 3 ) 2OH
Ic1.396C(CH 2 CH 3 )CH 2 CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ic1.397C(CH 2 CH 3 )CH 2 CH 3OClOH
Ic1.398C(CH 2 CH 3 )CH 2 CH 3OBrOH
Ic1.399C(CH 2 CH 3 )CH 2 CH 3ONO 2OH
Ic1.400C(CH 2 CH 3 )CH 2 CH 3OCHF 2OH
Ic1.401C(CH 2 CH 3 )CH 2 CH 3OCF 3OH
Ic1.402C(CH 2 CH 3 )CH 2 CH 3OOCH 3OH
Ic1.403C(CH 2 CH 3 )CH 2 CH 3OOCH 2 CH 3OH
Ic1.404C(CH 2 CH 3 )CH 2 CH 3OOCHF 2OH
Ic1.405C(CH 2 CH 3 )CH 2 CH 3OOCF 3OH
Ic1.406C(CH 2 CH 3 )CH 2 ClOSCH 3OH
Ic1.407C(CH 2 CH 3 )CH 2 ClOSCH 2 CH 3OH
Ic1.408C(CH 2 CH 3 )CH 2 ClOSO 2 CH 3OH
Ic1.409C(CH 2 CH 3 )CH 2 ClOSO 2 CH 2 CH 3OH
Ic1.410C(CH 2 CH 3 )CH 2 ClOSO 2 CH(CH 3 ) 2OH
Ic1.411C(CH 2 CH 3 )CH 2 ClOSO 2 (CH 2 ) 2 CH 3OH
Ic1.412C(CH 2 CH 3 )CH 2 ClOClOH
Ic1.413C(CH 2 CH 3 )CH 2 ClOBrOH
Ic1.414C(CH 2 CH 3 )CH 2 ClONO 2OH
Ic1.415C(CH 2 CH 3 )CH 2 ClOCHF 2OH
Ic1.416C(CH 2 CH 3 )CH 2 ClOCF 3OH
Ic1.417C(CH 2 CH 3 )CH 2 ClOOCH 3OH
Ic1.418C(CH 2 CH 3 )CH 2 ClOOCH 2 CH 3OH
Ic1.419C(CH 2 CH 3 )CH 2 ClOOCHF 2OH
Ic1.420C(CH 2 CH 3 )CH 2 ClOOCF 3OH
Ic1.421C(CH 2 CH 3 )HSSCH 3OH
Ic1.422C(CH 2 CH 3 )HSSCH 2 CH 3OH
Ic1.423C(CH 2 CH 3 )HSSO 2 CH 3OH
Ic1.424C(CH 2 CH 3 )HSSO 2 CH 2 CH 3OH
Ic1.425C(CH 2 CH 3 )HSSO 2 CH(CH 3 ) 2OH
Ic1.426C(CH 2 CH 3 )HSSO 2 (CH 2 ) 2 CH 3OH
Ic1.427C(CH 2 CH 3 )HSClOH
Ic1.428C(CH 2 CH 3 )HSBrOH
Ic1.429C(CH 2 CH 3 )HSNO 2OH
Ic1.430C(CH 2 CH 3 )HSCHF 2OH
Ic1.431C(CH 2 CH 3 )HSCF 3OH
Ic1.432C(CH 2 CH 3 )HSOCH 3OH
Ic1.433C(CH 2 CH 3 )HSOCH 2 CH 3OH
Ic1.434C(CH 2 CH 3 )HSOCHF 2OH
Ic1.435C(CH 2 CH 3 )HSOCF 3OH
Ic1.436C(CH 2 CH 3 )CH 3SSCH 3OH
Ic1.437C(CH 2 CH 3 )CH 3SSCH 2 CH 3OH
Ic1.438C(CH 2 CH 3 )CH 3SSO 2 CH 3OH
Ic1.439C(CH 2 CH 3 )CH 3SSO 2 CH 2 CH 3OH
Ic1.440C(CH 2 CH 3 )CH 3SSO 2 CH(CH 3 ) 2OH
Ic1.441C(CH 2 CH 3 )CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ic1.442C(CH 2 CH 3 )CH 3SClOH
Ic1.443C(CH 2 CH 3 )CH 3SBrOH
Ic1.444C(CH 2 CH 3 )CH 3SNO 2OH
Ic1.445C(CH 2 CH 3 )CH 3SCHF 2OH
Ic1.446C(CH 2 CH 3 )CH 3SCF 3OH
Ic1.447C(CH 2 CH 3 )CH 3SOCH 3OH
Ic1.448C(CH 2 CH 3 )CH 3SOCH 2 CH 3OH
Ic1.449C(CH 2 CH 3 )CH 3SOCHF 2OH
Ic1.450C(CH 2 CH 3 )CH 3SOCF 3OH
Ic1.451C(CH 2 CH 3 )CH 2 CH 3SSCH 3OH
Ic1.452C(CH 2 CH 3 )CH 2 CH 3SSCH 2 CH 3OH
Ic1.453C(CH 2 CH 3 )CH 2 CH 3SSO 2 CH 3OH
Ic1.454C(CH 2 CH 3 )CH 2 CH 3SSO 2 CH 2 CH 3OH
Ic1.455C(CH 2 CH 3 )CH 2 CH 3SSO 2 CH(CH 3 ) 2OH
Ic1.456C(CH 2 CH 3 )CH 2 CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ic1.457C(CH 2 CH 3 )CH 2 CH 3SClOH
Ic1.458C(CH 2 CH 3 )CH 2 CH 3SBrOH
Ic1.459C(CH 2 CH 3 )CH 2 CH 3SNO 2OH
Ic1.460C(CH 2 CH 3 )CH 2 CH 3SCHF 2OH
Ic1.461C(CH 2 CH 3 )CH 2 CH 3SCF 3OH
Ic1.462C(CH 2 CH 3 )CH 2 CH 3SOCH 3OH
Ic1.463C(CH 2 CH 3 )CH 2 CH 3SOCH 2 CH 3OH
Ic1.464C(CH 2 CH 3 )CH 2 CH 3SOCHF 2OH
Ic1.465C(CH 2 CH 3 )CH 2 CH 3SOCF 3OH
Ic1.466C(CH 2 CH 3 )CH 2 ClSSCH 3OH
Ic1.467C(CH 2 CH 3 )CH 2 ClSSCH 2 CH 3OH
Ic1.468C(CH 2 CH 3 )CH 2 ClSSO 2 CH 3OH
Ic1.469C(CH 2 CH 3 )CH 2 ClSSO 2 CH 2 CH 3OH
Ic1.470C(CH 2 CH 3 )CH 2 ClSSO 2 CH(CH 3 ) 2OH
Ic1.471C(CH 2 CH 3 )CH 2 ClSSO 2 (CH 2 ) 2 CH 3OH
Ic1.472C(CH 2 CH 3 )CH 2 ClSClOH
Ic1.473C(CH 2 CH 3 )CH 2 ClSBrOH
Ic1.474C(CH 2 CH 3 )CH 2 ClSNO 2OH
Ic1.475C(CH 2 CH 3 )CH 2 ClSCHF 2OH
Ic1.476C(CH 2 CH 3 )CH 2 ClSCF 3OH
Ic1.477C(CH 2 CH 3 )CH 2 ClSOCH 3OH
Ic1.478C(CH 2 CH 3 )CH 2 ClSOCH 2 CH 3OH
Ic1.479C(CH 2 CH 3 )CH 2 ClSOCHF 2OH
Ic1.480C(CH 2 CH 3 )CH 2 ClSOCF 3OH
Ic1.481C(CH 2 CH 3 )HNCH 3SCH 3OH
Ic1.482C(CH 2 CH 3 )HNCH 3SCH 2 CH 3OH
Ic1.483C(CH 2 CH 3 )HNCH 3SO 2 CH 3OH
Ic1.484C(CH 2 CH 3 )HNCH 3SO 2 CH 2 CH 3OH
Ic1.485C(CH 2 CH 3 )HNCH 3SO 2 CH(CH 3 ) 2OH
Ic1.486C(CH 2 CH 3 )HNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.487C(CH 2 CH 3 )HNCH 3ClOH
Ic1.488C(CH 2 CH 3 )HNCH 3BrOH
Ic1.489C(CH 2 CH 3 )HNCH 3NO 2OH
Ic1.490C(CH 2 CH 3 )HNCH 3CHF 2OH
Ic1.491C(CH 2 CH 3 )HNCH 3CF 3OH
Ic1.492C(CH 2 CH 3 )HNCH 3OCH 3OH
Ic1.493C(CH 2 CH 3 )HNCH 3OCH 2 CH 3OH
Ic1.494C(CH 2 CH 3 )HNCH 3OCHF 2OH
Ic1.495C(CH 2 CH 3 )HNCH 3OCF 3OH
Ic1.496C(CH 2 CH 3 )CH 3NCH 3SCH 3OH
Ic1.497C(CH 2 CH 3 )CH 3NCH 3SCH 2 CH 3OH
Ic1.498C(CH 2 CH 3 )CH 3NCH 3SO 2 CH 3OH
Ic1.499C(CH 2 CH 3 )CH 3NCH 3SO 2 CH 2 CH 3OH
Ic1.500C(CH 2 CH 3 )CH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ic1.501C(CH 2 CH 3 )CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.502C(CH 2 CH 3 )CH 3NCH 3ClOH
Ic1.503C(CH 2 CH 3 )CH 3NCH 3BrOH
Ic1.504C(CH 2 CH 3 )CH 3NCH 3NO 2OH
Ic1.505C(CH 2 CH 3 )CH 3NCH 3CHF 2OH
Ic1.506C(CH 2 CH 3 )CH 3NCH 3CF 3OH
Ic1.507C(CH 2 CH 3 )CH 3NCH 3OCH 3OH
Ic1.508C(CH 2 CH 3 )CH 3NCH 3OCH 2 CH 3OH
Ic1.509C(CH 2 CH 3 )CH 3NCH 3OCHF 2OH
Ic1.510C(CH 2 CH 3 )CH 3NCH 3OCF 3OH
Ic1.511C(CH 2 CH 3 )CH 2 CH 3NCH 3SCH 3OH
Ic1.512C(CH 2 CH 3 )CH 2 CH 3NCH 3SCH 2 CH 3OH
Ic1.513C(CH 2 CH 3 )CH 2 CH 3NCH 3SO 2 CH 3OH
Ic1.514C(CH 2 CH 3 )CH 2 CH 3NCH 3SO 2 CH 2 CH 3OH
Ic1.515C(CH 2 CH 3 )CH 2 CH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ic1.516C(CH 2 CH 3 )CH 2 CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.517C(CH 2 CH 3 )CH 2 CH 3NCH 3ClOH
Ic1.518C(CH 2 CH 3 )CH 2 CH 3NCH 3BrOH
Ic1.519C(CH 2 CH 3 )CH 2 CH 3NCH 3NO 2OH
Ic1.520C(CH 2 CH 3 )CH 2 CH 3NCH 3CHF 2OH
Ic1.521C(CH 2 CH 3 )CH 2 CH 3NCH 3CF 3OH
Ic1.522C(CH 2 CH 3 )CH 2 CH 3NCH 3OCH 3OH
Ic1.523C(CH 2 CH 3 )CH 2 CH 3NCH 3OCH 2 CH 3OH
Ic1.524C(CH 2 CH 3 )CH 2 CH 3NCH 3OCHF 2OH
Ic1.525C(CH 2 CH 3 )CH 2 CH 3NCH 3OCF 3OH
Ic1.526C(CH 2 CH 3 )CH 2 ClNCH 3SCH 3OH
Ic1.527C(CH 2 CH 3 )CH 2 ClNCH 3SCH 2 CH 3OH
Ic1.528C(CH 2 CH 3 )CH 2 ClNCH 3SO 2 CH 3OH
Ic1.529C(CH 2 CH 3 )CH 2 ClNCH 3SO 2 CH 2 CH 3OH
Ic1.530C(CH 2 CH 3 )CH 2 ClNCH 3SO 2 CH(CH 3 ) 2OH
Ic1.531C(CH 2 CH 3 )CH 2 ClNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.532C(CH 2 CH 3 )CH 2 ClNCH 3ClOH
Ic1.533C(CH 2 CH 3 )CH 2 ClNCH 3BrOH
Ic1.534C(CH 2 CH 3 )CH 2 ClNCH 3NO 2OH
Ic1.535C(CH 2 CH 3 )CH 2 ClNCH 3CHF 2OH
Ic1.536C(CH 2 CH 3 )CH 2 ClNCH 3CF 3OH
Ic1.537C(CH 2 CH 3 )CH 2 ClNCH 3OCH 3OH
Ic1.538C(CH 2 CH 3 )CH 2 ClNCH 3OCH 2 CH 3OH
Ic1.539C(CH 2 CH 3 )CH 2 ClNCH 3OCHF 2OH
Ic1.540C(CH 2 CH 3 )CH 2 ClNCH 3OCF 3OH
Ic1.541NHOSCH 3OH
Ic1.542NHOSCH 2 CH 3OH
Ic1.543NHOSO 2 CH 3OH
Ic1.544NHOSO 2 CH 2 CH 3OH
Ic1.545NHOSO 2 CH(CH 3 ) 2OH
Ic1.546NHOSO 2 (CH 2 ) 2 CH 3OH
Ic1.547NHOClOH
Ic1.548NHOBrOH
Ic1.549NHONO 2OH
Ic1.550NHOCHF 2OH
Ic1.551NHOCF 3OH
Ic1.552NHOOCH 3OH
Ic1.553NHOOCH 2 CH 3OH
Ic1.554NHOOCHF 2OH
Ic1.555NHOOCF 3OH
Ic1.556NCH 3OSCH 3OH
Ic1.557NCH 3OSCH 2 CH 3OH
Ic1.558NCH 3OSO 2 CH 3OH
Ic1.559NCH 3OSO 2 CH 2 CH 3OH
Ic1.560NCH 3OSO 2 CH(CH 3 ) 2OH
Ic1.561NCH 3OSO 2 (CH 2 ) 2 CH 3OH
Ic1.562NCH 3OClOH
Ic1.563NCH 3OBrOH
Ic1.564NCH 3ONO 2OH
Ic1.565NCH 3OCHF 2OH
Ic1.566HCH 3OCF 3OH
Ic1.567NCH 3OOCH 3OH
Ic1.568NCH 3OOCH 2 CH 3OH
Ic1.569NCH 3OOCHF 2OH
Ic1.570NCH 3OOCF 3OH
Ic1.571NCH 2 CH 3OSCH 3OH
Ic1.572NCH 2 CH 3OSCH 2 CH 3OH
Ic1.573NCH 2 CH 3OSO 2 CH 3OH
Ic1.574NCH 2 CH 3OSO 2 CH 2 CH 3OH
Ic1.575NCH 2 CH 3OSO 2 CH(CH 3 ) 2OH
Ic1.576NCH 2 CH 3OSO 2 (CH 2 ) 2 CH 3OH
Ic1.577NCH 2 CH 3OClOH
Ic1.578NCH 2 CH 3OBrOH
Ic1.579NCH 2 CH 3ONO 2OH
Ic1.580NCH 2 CH 3OCHF 2OH
Ic1.581NCH 2 CH 3OCF 3OH
Ic1.582NCH 2 CH 3OOCH 3OH
Ic1.583NCH 2 CH 3OOCH 2 CH 3OH
Ic1.584NCH 2 CH 3OOCHF 2OH
Ic1.585NCH 2 CH 3OOCF 3OH
Ic1.586NCH 2 ClOSCH 3OH
Ic1.587NCH 2 ClOSCH 2 CH 3OH
Ic1.588NCH 2 ClOSO 2 CH 3OH
Ic1.589NCH 2 ClOSO 2 CH 2 CH 3OH
Ic1.590NCH 2 ClOSO 2 CH(CH 3 ) 2OH
Ic1.591NCH 2 ClOSO 2 (CH 2 ) 2 CH 3OH
Ic1.592NCH 2 ClOClOH
Ic1.593NCH 2 ClOBrOH
Ic1.594NCH 2 ClONO 2OH
Ic1.595NCH 2 ClOCHF 2OH
Ic1.596NCH 2 ClOCF 3OH
Ic1.597NCH 2 ClOOCH 3OH
Ic1.598NCH 2 ClOOCH 2 CH 3OH
Ic1.599NCH 2 ClOOCHF 2OH
Ic1.600NCH 2 ClOOCF 3OH
Ic1.601NHSSCH 3OH
Ic1.602NHSSCH 2 CH 3OH
Ic1.603NHSSO 2 CH 3OH
Ic1.604NHSSO 2 CH 2 CH 3OH
Ic1.605NHSSO 2 CH(CH 3 ) 2OH
Ic1.606NHSSO 2 (CH 2 ) 2 CH 3OH
Ic1.607NHSClOH
Ic1.608NHSBrOH
Ic1.609NHSNO 2OH
Ic1.610NHSCHF 2OH
Ic1.611NHSCF 3OH
Ic1.612NHSOCH 3OH
Ic1.613NHSOCH 2 CH 3OH
Ic1.614NHSOCHF 2OH
Ic1.615NHSOCF 3OH
Ic1.616NCH 3SSCH 3OH
Ic1.617NCH 3SSCH 2 CH 3OH
Ic1.618NCH 3SSO 2 CH 3OH
Ic1.619NCH 3SSO 2 CH 2 CH 3OH
Ic1.620NCH 3SSO 2 CH(CH 3 ) 2OH
Ic1.621NCH 3SSO 2 (CH 2 ) 2 CH 3OH
Ic1.622NCH 3SClOH
Ic1.623NCH 3SBrOH
Ic1.624NCH 3SNO 2OH
Ic1.625NCH 3SCHF 2OH
Ic1.626NCH 3SCF 3OH
Ic1.627NCH 3SOCH 3OH
Ic1.628NCH 3SOCH 2 CH 3OH
Ic1.629NCH 3SOCHF 2OH
Ic1.630NCH 3SOCF 3OH
Ic1.631NCH 2 CH 3SSCH 3OH
Ic1.632NCH 2 CH 3SSCH 2 CH 3OH
Ic1.633NCH 2 CH 3SSO 2 CH 3OH
Ic1.634NCH 2 CH 3SSO 2 CH 2 CH 3OH
Ic1.635NCH 2 CH 3SSO 2 CH(CH 3 ) 2OH
Ic1.636NCH 2 CH 3SSO 2 (CH 2 ) 2 CH 3OH
Ic1.637NCH 2 CH 3SClOH
Ic1.638NCH 2 CH 3SBrOH
Ic1.639NCH 2 CH 3SNO 2OH
Ic1.640NCH 2 CH 3SCHF 2OH
Ic1.641NCH 2 CH 3SCF 3OH
Ic1.642NCH 2 CH 3SOCH 3OH
Ic1.643NCH 2 CH 3SOCH 2 CH 3OH
Ic1.644NCH 2 CH 3SOCHF 2OH
Ic1.645NCH 2 CH 3SOCF 3OH
Ic1.646NCH 2 ClSSCH 3OH
Ic1.647NCH 2 ClSSCH 2 CH 3OH
Ic1.648NCH 2 ClSSO 2 CH 3OH
Ic1.649NCH 2 ClSSO 2 CH 2 CH 3OH
Ic1.650NCH 2 ClSSO 2 CH(CH 3 ) 2OH
Ic1.651NCH 2 ClSSO 2 (CH 2 ) 2 CH 3OH
Ic1.652NCH 2 ClSClOH
Ic1.653NCH 2 ClSBrOH
Ic1.654NCH 2 ClSNO 2OH
Ic1.655NCH 2 ClSCHF 2OH
Ic1.656HCH 2 ClSCF 3OH
Ic1.657NCH 2 ClSOCH 3OH
Ic1.658NCH 2 ClSOCH 2 CH 3OH
Ic1.659NCH 2 ClSOCHF 2OH
Ic1.660NCH 2 ClSOCF 3OH
Ic1.661NHNCH 3SCH 3OH
Ic1.662NHNCH 3SCH 2 CH 3OH
Ic1.663NHNCH 3SO 2 CH 3OH
Ic1.664NHNCH 3SO 2 CH 2 CH 3OH
Ic1.665NHNCH 3SO 2 CH(CH 3 ) 2OH
Ic1.666NHNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.667NHNCH 3ClOH
Ic1.668NHNCH 3BrOH
Ic1.669NHNCH 3NO 2OH
Ic1.670NHNCH 3CHF 2OH
Ic1.671NHNCH 3CF 3OH
Ic1.672NHNCH 3OCH 3OH
Ic1.673NHNCH 3OCH 2 CH 3OH
Ic1.674NHNCH 3OCHF 2OH
Ic1.675NHNCH 3OCF 3OH
Ic1.676NCH 3NCH 3SCH 3OH
Ic1.677NCH 3NCH 3SCH 2 CH 3OH
Ic1.678NCH 3NCH 3SO 2 CH 3OH
Ic1.679NCH 3NCH 3SO 2 CH 2 CH 3OH
Ic1.680NCH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ic1.681NCH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.682NCH 3NCH 3ClOH
Ic1.683NCH 3NCH 3BrOH
Ic1.684NCH 3NCH 3NO 2OH
Ic1.685NCH 3NCH 3CHF 2OH
Ic1.686NCH 3NCH 3CF 3OH
Ic1.687NCH 3NCH 3OCH 3OH
Ic1.688NCH 3NCH 3OCH 2 CH 3OH
Ic1.689NCH 3NCH 3OCHF 2OH
Ic1.690NCH 3NCH 3OCF 3OH
Ic1.691NCH 2 CH 3NCH 3SCH 3OH
Ic1.692NCH 2 CH 3NCH 3SCH 2 CH 3OH
Ic1.693NCH 2 CH 3NCH 3SO 2 CH 3OH
Ic1.694NCH 2 CH 3NCH 3SO 2 CH 2 CH 3OH
Ic1.695NCH 2 CH 3NCH 3SO 2 CH(CH 3 ) 2OH
Ic1.696NCH 2 CH 3NCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.697NCH 2 CH 3NCH 3ClOH
Ic1.698NCH 2 CH 3NCH 3BrOH
Ic1.699NCH 2 CH 3NCH 3NO 2OH
Ic1.700NCH 2 CH 3NCH 3CHF 2OH
Ic1.701NCH 2 CH 3NCH 3CF 3OH
Ic1.702NCH 2 CH 3NCH 3OCH 3OH
Ic1.703NCH 2 CH 3NCH 3OCH 2 CH 3OH
Ic1.704NCH 2 CH 3NCH 3OCHF 2OH
Ic1.705NCH 2 CH 3NCH 3OCF 3OH
Ic1.706NCH 2 ClNCH 3SCH 3OH
Ic1.707NCH 2 ClNCH 3SCH 2 CH 3OH
Ic1.708NCH 2 ClNCH 3SO 2 CH 3OH
Ic1.709NCH 2 ClNCH 3SO 2 CH 2 CH 3OH
Ic1.710NCH 2 ClNCH 3SO 2 CH(CH 3 ) 2OH
Ic1.711NCH 2 ClNCH 3SO 2 (CH 2 ) 2 CH 3OH
Ic1.712NCH 2 ClNCH 3ClOH
Ic1.713NCH 2 ClNCH 3BrOH
Ic1.714NCH 2 ClNCH 3NO 2OH
Ic1.715NCH 2 ClNCH 3CHF 2OH
Ic1.716NCH 2 ClNCH 3CF 3OH
Ic1.717NCH 2 ClNCH 3OCH 3OH
Ic1.718NCH 2 ClNCH 3OCH 2 CH 3OH
Ic1.719NCH 2 ClNCH 3OCHF 2OH
Ic1.720NCH 2 ClNCH 3OCF 3OH
TABLE 4 — physical data m.p. [° C.];
No.R 1R 2R 3YR 4R 12R 13R 141 H-NMR [δ in ppm]
4.1ClHHCH 2SO 2 CH 3OHcyclopentylH192-197
4.2ClHHCH 2SO 2 CH 3OCOC 6 H 5cyclopentylH235-240
4.3ClHHCH 2SO 2 CH 3OCO(3-F—C 6 H 4 )cyclopentylH220-225
4.4ClHHCH 2SO 2 CH 3OCH 3cyclopentylH195-200
4.5ClHHCH 2SO 2 CH 3OCH 2 CH 3cyclopentylH145-150
4.6CH 3HHCH 2SO 2 CH 3OHcyclopentylH135-140
4.7CH 3HHCH 2SO 2 CH 3OCO(3-F—C 6 H 4 )cyclopentylH1.4-2.0 (m, 8H); 2.0(s, 3H); 3.2
(m, 2H); 4.4(m, 2H); 4.8(m, 1H);
7.6-7.8(m, 7H)
4.8CH 3HHCH 2SO 2 CH 3OCH(CH 3 ) 2cyclopentylH1.2 (d, 6H); 1.4-2.0(m, 8H); 2.7
(s, 3H); 2.9(s, 3H); 3.3(br, 2H); 4.5
(t, 2H), 4.8(br, 1H); 4.9(m, 1H); 7.5
(s, 1H); 7.7(d, 1H); 7.9(d, 1H)
4.9ClHHCH 2SO 2 CH 3OH2-norbornylH135-140
4.10CH 3HHCH 2SO 2 CH 3OH2-norbornylH110-115
4.11ClHHCH 2SO 2 CH 3OCOC 6 H 52-norbornylH200-205
4.12ClHHCH 2SO 2 CH 3OCO(3-F—C 6 H 4 )2-norbornylH85-90
4.13CH 3HHCH 2SO 2 CH 3OCOC 6 H 52-norbornylH1.0-2.5(m, 10H); 2.1(s, 3H); 3.0
(s, 3H); 3.2(t, 2H); 4.2-4.7(m, 3H);
7.4-8.2(m, 8H)
4.14CH 3HHCH 2SO 2 CH 3OCO(3-F—C 6 H 4 )2-norbornylH1.0-2.6(m, 10H); 2.1(s, 3H); 3.01
(s, 3H); 3.21(t, 2H), 4.3-4.7(m, 3H);
7.4-8.0(m, 7H)
4.15ClHHCH 2SO 2 CH 3OH2-adamantylH120-125
4.16CH 3HHCH 2SO 2 CH 3OH2-adamantylH140-145
4.17ClHHCH 2SO 2 CH 3OHcyclopropylH227-228
4.19OCH 3HHCH 2SO 2 CH 3OHcyclopropylH197-199
4.19ClHHCH 2SO 2 CH 3OSO 2 (4-CH 3 —C 6 H 4 )cyclopropylH81-82
4.20ClHHCH 2SO 2 CH 3OCH(CH 3 ) 2cyclopropylH179-190
4.21ClHHCH 2SO 2 CH 3OCOC 6 H 5cyclopropylHoil
4.22ClHHCH 2SO 2 CH 3OCO(3-F—C 6 H 4 )cyclopropylH198-200
4.23OCH 3HHCH 2SO 2 CH 3OHcyclopropylH160-161
4.24CH 3HHCH 2SO 2 CH 3OHcyclopropylH178-179
12 of 15 part labels are ours — the grant heads the rest

Claims

7 · 1 independent · depth 2
1234567
7 granted claims

Classifications

11 codes
IPC · International Patent Classification
Section A — Human necessities
  • A01N43/74
  • A01N43/78
  • A01N43/80
  • A01N43/56
Section C — Chemistry; metallurgy
  • C07D413/10
  • C07D417/10
  • C07D403/10
  • C07B61/00
  • C07D231/12
USPC · US Patent Classification
504/271548/247

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Alan L. Rotman
art unit 1626 · TC 1600
Citations: 7 back · 1 forward

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Worldwide family

14 members · 10 offices
US1EP2JP2WO1AR1AT1AU1BR2CA2DE1
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DOCDB simple family 7917033
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›IP5 & PCT — 6 members
OfficePublicationKindPublishedFiledStatusTitle
USthis patentUS-6713436-B1B130 Mar 20041 Dec 1999granted1-cycloalkylpyrazolyl-benzoyl derivatives
EPEP-1200429-A1A12 May 20021 Dec 1999publishedDerives de 1-cycloalkylpyrazolyl-benzoylefr
EPEP-1200429-B1B116 Jun 20041 Dec 1999grantedDerives de 1-cycloalkylpyrazolyl-benzoylefr
JPJP-2003506450-AA18 Feb 20031 Dec 1999published1−シクロアルキルピラゾリルベンゾイル誘導体ja
JPJP-4116291-B2B29 Jul 20081 Dec 1999granted1−シクロアルキルピラゾリルベンゾイル誘導体ja
WOWO-0110864-A1A115 Feb 20011 Dec 1999publishedDerives de 1-cycloalkylpyrazolyl-benzoylefr
›Other offices — 8 members
OfficePublicationKindPublishedFiledStatusTitle
ARAR-024845-A1A130 Oct 200230 Nov 1999publishedDerivados de 1-cicloalquilpirazolil-benzoilo y sus sales, procedimiento para obtener dichos derivados, las composiciones herbicidas que los contienen y supreparacion, el procedimiento para controlar el crecimiento de plantas indeseadas con dichos derivados y el uso de dichos derivados como herbicidaes
ATAT-E269328-T1T115 Jul 20041 Dec 1999granted1-cycloalkylpyrazolyl-benzoyl-derivatede
AUAU-1558300-AA5 Mar 20011 Dec 1999published1-cycloalkylpyrazoyl-benzoyl derivatives
BRBR-9917431-AA23 Apr 20021 Dec 1999publishedDerivado de 1-cicloalquilpirazolilbenzoìla, composição, processos para preparar derivados de 1-cicloalquilpirazolilbenzoìla e para preparar composições, método para controlar a vegetação não desejada, e, uso dos derivados de 1-cicloalquilpirazolilbenzoìlapt
BRBR-9917431-B1B18 Sep 20101 Dec 1999publishedderivado de 1-cicloalquilpirazolilbenzoìla, composição, processos para preparar derivados de 1-cicloalquilpirazolilbenzoìla e para preparar composições, método para controlar a vegetação não desejada, e, uso dos derivados de 1-cicloalquilpirazolilbenzoìla.pt
CACA-2381243-A1A115 Feb 20011 Dec 1999published1-cycloalkylpyrazoyl-benzoyl derivatives
CACA-2381243-CC7 Apr 20091 Dec 1999granted1-cycloalkylpyrazoyl-benzoyl derivatives
DEDE-59909774-D1D122 Jul 20041 Dec 1999granted1-cycloalkylpyrazolyl-benzoyl-derivatede

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